HTH / Hilltop Holdings Inc. - Pemfailan SEC, Laporan Tahunan, Penyata Proksi

Hilltop Holdings Inc.
US ˙ NYSE ˙ US4327481010

Statistik Asas
LEI 54930010TA543US0PM65
CIK 1265131
SEC Filings
All companies that sell securities in the United States must register with the Securities and Exchange Commission (SEC) and file reports on a regular basis. These reports include company annual reports (10K, 10Q), news updates (8K), investor presentations (found in 8Ks), insider trades (form 4), ownership reports (13D, and 13G), and reports related to the specific securities sold, such as registration statements and prospectus. This page shows recent SEC filings related to Hilltop Holdings Inc.
SEC Filings (Chronological Order)
Halaman ini menyediakan senarai kronologi lengkap bagi Pemfailan SEC, tidak termasuk pemfailan pemilikan yang kami sediakan di tempat lain.
August 29, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 27, 2025 Hilltop Holdings

Common Stock, par value $0.01 per share HTH UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 27, 2025 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other ju

August 14, 2025 8-A12B

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-A FOR REGISTRATION OF CERTAIN CLASSES OF SECURITIES PURSUANT TO SECTION 12(b) OR (g) OF THE SECURITIES EXCHANGE ACT OF 1934 Hilltop Holdings Inc. (Exact name of registrant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-A FOR REGISTRATION OF CERTAIN CLASSES OF SECURITIES PURSUANT TO SECTION 12(b) OR (g) OF THE SECURITIES EXCHANGE ACT OF 1934 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 84-1477939 (State or other jurisdiction of incorporation or organization) (IRS Employer Identification No.) 656

August 14, 2025 CERT

NYSE TEXAS CERTIFICATION

New York Stock Exchange 11 Wall Street New York, NY 10005 Tel: +1 212.656.3000 nyse.com August 14, 2025 Chief, Information Technology Securities and Exchange Commission Division of Corporate Finance 100 F Street, NE MS 3040 Washington, DC 20549 To whom it may concern: The NYSE Texas certifies its approval for listing and registration of the Common Stock, par value $0.01 per share, of Hilltop Holdi

July 29, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 24, 2025 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission File

July 25, 2025 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2025 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Commission File Number: 1-31987 Hilltop Holdings Inc.

July 24, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 24, 2025 Hilltop Holdings In

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 24, 2025 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission File

July 24, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 24, 2025 Hilltop Holdings In

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 24, 2025 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission File

July 24, 2025 EX-99.1

Q2 2025 3 Investor Highlights – Notes: (1) Average Bank Loans HFI reflect consolidated loans held for investment excluding margin loans from the Broker-Dealer business. • PlainsCapital Bank generated $54.9 million in pre-tax income during Q2 2025 • B

Exhibit 99.1 Hilltop Holdings Inc. Q2 2025 Earnings Presentation July 25, 2025 Preface 2 Corporate Headquarters Additional Information 6565 Hillcrest Ave Dallas, TX 75205 Phone: 214-855-2177 www.hilltop.com Please Contact: Matt Dunn Phone: 214-525-4636 Email: [email protected] FORWARD-LOOKING STATEMENTS This presentation and statements made by representatives of Hilltop Holdings Inc. (“Hilltop” or

July 24, 2025 EX-99.1

June 30,

Exhibit 99.1 Investor Relations Contact: Matt Dunn 214-525-4636 [email protected] Hilltop Holdings Inc. Announces Financial Results for Second Quarter 2025 DALLAS — (BUSINESS WIRE) July 24, 2025 — Hilltop Holdings Inc. (NYSE: HTH) (“Hilltop”) today announced financial results for the second quarter of 2025. Hilltop produced income to common stockholders of $36.1 million, or $0.57 per diluted share

May 16, 2025 8-K

Termination of a Material Definitive Agreement, Triggering Events That Accelerate or Increase a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 15, 2025 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission File N

April 30, 2025 DEF 14A

UNITED STATES

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14

April 30, 2025 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 29, 2025 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission File

April 30, 2025 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ⌧ Filed by a Party other than the Registrant ◻ Check the appropriate box: ◻ Preliminary Proxy Statement ◻ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ◻ Defin

April 28, 2025 EX-19.1

Insider Trading Policy.

Exhibit 19.1 INSIDER TRADING POLICY This Insider Trading Policy (this “Policy”) sets forth the policy for directors, officers and other employees (for purposes of this Policy, employees shall include consultants) of Hilltop Holdings Inc. (“Hilltop”) and its subsidiaries (collectively, the “Company”) with respect to transactions in Hilltop’s securities. Applicability of Policy This Policy applies t

April 28, 2025 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2025 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Commission File Number: 1-31987 Hilltop Holdings Inc.

April 25, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 24, 2025 Hilltop Holdings I

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 24, 2025 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission File

April 25, 2025 EX-10.7(3)

Second Amendment to Employment Agreement by and between Hilltop Holdings Inc. and Martin B. Winges, dated April 25, 2025, but effective as of February 19, 2025.

EXHIBIT 10.7.3 SECOND AMENDMENT TO EMPLOYMENT AGREEMENT THIS SECOND AMENDMENT TO EMPLOYMENT AGREEMENT (this “Amendment”) is made and entered into as of April 25, 2025 (the “Execution Date”), but effective as of February 19, 2025, by and between Hilltop Holdings Inc. (the “Company”), on behalf of itself and all of its subsidiaries (collectively, “Employer”), and Martin B. Winges (“Executive”). Each

April 24, 2025 EX-99.1

Q1 2025 3 Investor Highlights – Notes: (1) Average Bank Loans HFI reflect consolidated loans held for investment excluding margin loans from the Broker-Dealer business. • PlainsCapital Bank generated $40.1 million in pre-tax income during Q1 2025 • B

Exhibit 99.1 Hilltop Holdings Inc. Q1 2025 Earnings Presentation April 25, 2025 Preface 2 Corporate Headquarters Additional Information 6565 Hillcrest Ave Dallas, TX 75205 Phone: 214-855-2177 www.hilltop.com Please Contact: Matt Dunn Phone: 214-525-4636 Email: [email protected] FORWARD-LOOKING STATEMENTS This presentation and statements made by representatives of Hilltop Holdings Inc. (“Hilltop” o

April 24, 2025 EX-99.1

March 31,

Exhibit 99.1 Investor Relations Contact: Matt Dunn 214-525-4636 [email protected] Hilltop Holdings Inc. Announces Financial Results for First Quarter 2025 DALLAS — (BUSINESS WIRE) April 24, 2025 — Hilltop Holdings Inc. (NYSE: HTH) (“Hilltop”) today announced financial results for the first quarter of 2025. Hilltop produced income to common stockholders of $42.1 million, or $0.65 per diluted share,

April 24, 2025 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 24, 2025 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission File

April 24, 2025 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 24, 2025 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission File

April 23, 2025 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 19, 2025 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission File

February 24, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 24, 2025 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission F

February 14, 2025 EX-97

Incentive Compensation Clawback Policy

Exhibit 97 INCENTIVE COMPENSATION CLAWBACK POLICY OVERVIEW The Board of Directors (“Board”) of Hilltop Holdings Inc.

February 14, 2025 EX-21.1

List of subsidiaries of the Registrant.

Exhibit 21.1 List of Subsidiaries of Hilltop Holdings Inc. As of February 14, 2025 Name State or Other Jurisdiction of Incorporation or Formation ARC Insurance Holdings, Inc. Delaware First Southwest Holdings LLC Delaware First Southwest Capital Investments, Inc. Delaware First Southwest Leasing Company Delaware FSC Asset Administrator, LLC Delaware Highland HomeLoans, LLC Delaware Hilltop Investm

February 14, 2025 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended: December 31, 2024 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 1-31987 Hilltop Hol

February 14, 2025 EX-19.1

Insider Trading Policy.

Exhibit 19.1 INSIDER TRADING POLICY This Insider Trading Policy (the “Policy”) sets forth the policy for directors, officers and other employees (for purposes of this Policy, employees shall include consultants) of Hilltop Holdings Inc. (“Hilltop”) and its subsidiaries (collectively, the “Company”) with respect to transactions in Hilltop’s securities. Applicability of Policy This Policy applies to

January 30, 2025 EX-99.1

Q4 2024 3 Investor Highlights – Notes: (1) Average Bank Loans HFI reflect consolidated loans held for investment excluding margin loans from the Broker-Dealer business. • PlainsCapital Bank generated $50.6 million in pre-tax income. The quarter inclu

Exhibit 99.1 Hilltop Holdings Inc. Q4 2024Earnings Presentation January 31, 2025 Preface 2 Corporate Headquarters Additional Information 6565 Hillcrest Ave Dallas, TX 75205 Phone: 214-855-2177 www.hilltop.com Please Contact: Matt Dunn Phone: 214-525-4636 Email: [email protected] FORWARD-LOOKING STATEMENTS This presentation and statements made by representatives of Hilltop Holdings Inc. (“Hilltop”

January 30, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 30, 2025 Hilltop Holdings

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 30, 2025 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission Fi

January 30, 2025 EX-99.1

December 31,

EX-99.1 2 hth-20250130xex99d1.htm EX-99.1 Exhibit 99.1 Investor Relations Contact: Matt Dunn 214-525-4636 [email protected] Hilltop Holdings Inc. Announces Financial Results for Fourth Quarter and Full Year 2024 DALLAS — (BUSINESS WIRE) January 30, 2025 — Hilltop Holdings Inc. (NYSE: HTH) (“Hilltop”) today announced financial results for the fourth quarter and full year 2024. Hilltop produced inco

January 30, 2025 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 30, 2025 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission Fi

January 27, 2025 EX-99.1

Hilltop Opportunity Partners Announces Agreement to Sell its interest in Moser Energy Systems

Exhibit 99.1 Investor Relations Contact: Matt Dunn 214-525-4636 [email protected] Hilltop Opportunity Partners Announces Agreement to Sell its interest in Moser Energy Systems DALLAS — (BUSINESS WIRE) January 27, 2025 — Hilltop Opportunity Partners, the merchant bank subsidiary of Hilltop Holdings Inc. (NYSE: HTH), today announced that its portfolio company, Moser Holdings, LLC, entered into a def

January 27, 2025 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 27, 2025 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission Fi

January 23, 2025 EX-4.8

Indenture, dated as of September 25, 2024, by and between Hilltop Securities Inc. and The Bank of New York Mellon, as indenture trustee.

Exhibit 4.8 Execution Version HILLTOP SECURITIES INC. Issuer THE BANK OF NEW YORK MELLON Trustee INDENTURE Dated as of September 25, 2024 SECURED COMMERCIAL PAPER NOTES, SERIES 2024-1 TABLE OF CONTENTS Page Article I. DEFINITIONS AND CONSTRUCTION 2 Section 1.01 Definitions 2 Section 1.02 Rules of Construction 7 Section 1.03 Supplemental Indentures Controlling 8 Article II. THE SERIES 2024-1 CP NOT

January 23, 2025 8-K

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 21, 2025 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission Fi

January 16, 2025 8-K

Termination of a Material Definitive Agreement, Triggering Events That Accelerate or Increase a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 15, 2025 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission Fi

October 25, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2024 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Commission File Number: 1-31987 Hilltop Holdings Inc.

October 24, 2024 EX-99.1

Q3 2024 3 Investor Highlights – Notes: (1) Average Bank Loans HFI reflect consolidated loans held for investment excluding margin loans from the Broker-Dealer business. • PlainsCapital Bank generated $48.1 million in pre-tax income during Q3 2024 • B

Exhibit 99.1 Hilltop Holdings Inc. Q3 2024Earnings Presentation October 25, 2024 Preface 2 Corporate Headquarters Additional Information 6565 Hillcrest Ave Dallas, TX 75205 Phone: 214-855-2177 www.hilltop.com Please Contact: Matt Dunn Phone: 214-525-4636 Email: [email protected] FORWARD-LOOKING STATEMENTS This presentation and statements made by representatives of Hilltop Holdings Inc. (“Hilltop”

October 24, 2024 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): October 24, 2024 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission Fi

October 24, 2024 EX-99.1

September 30,

Exhibit 99.1 Investor Relations Contact: Matt Dunn 214-525-4636 [email protected] Hilltop Holdings Inc. Announces Financial Results for Third Quarter 2024 DALLAS — (BUSINESS WIRE) October 24, 2024 — Hilltop Holdings Inc. (NYSE: HTH) (“Hilltop”) today announced financial results for the third quarter of 2024. Hilltop produced income to common stockholders of $29.7 million, or $0.46 per diluted shar

October 24, 2024 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): October 24, 2024 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission Fi

August 2, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2024 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Commission File Number: 1-31987 Hilltop Holdings Inc.

July 29, 2024 8-K

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 25, 2024 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission File

July 25, 2024 EX-99.1

Q2 2024 3 Investor Highlights – Notes: (1) Return on average assets is defined as consolidated net income before noncontrolling interest divided by average assets. (2) Average Bank Loans HFI reflect consolidated loans held for investment excluding ma

Exhibit 99.1 Hilltop Holdings Inc. Q2 2024Earnings Presentation July 26, 2024 Preface 2 Corporate Headquarters Additional Information 6565 Hillcrest Ave Dallas, TX 75205 Phone: 214-855-2177 www.hilltop.com Please Contact: Matt Dunn Phone: 214-525-4636 Email: [email protected] FORWARD-LOOKING STATEMENTS This presentation and statements made by representatives of Hilltop Holdings Inc. (“Hilltop” or

July 25, 2024 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 25, 2024 Hilltop Holdings In

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 25, 2024 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission File

July 25, 2024 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 25, 2024 Hilltop Holdings In

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 25, 2024 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission File

July 25, 2024 EX-99.1

June 30,

Exhibit 99.1 Investor Relations Contact: Matt Dunn 214-525-4636 [email protected] Hilltop Holdings Inc. Announces Financial Results for Second Quarter 2024 DALLAS — (BUSINESS WIRE) July 25, 2024 — Hilltop Holdings Inc. (NYSE: HTH) (“Hilltop”) today announced financial results for the second quarter of 2024. Hilltop produced income to common stockholders of $20.3 million, or $0.31 per diluted share

May 3, 2024 EX-10.1

Transition and Release Agreement by and between Hilltop Holdings Inc. and Jerry L. Schaffner, dated as of May 1, 2024.

EXHIBIT 10.1 TRANSITION AND RELEASE AGREEMENT This Transition and Release Agreement (this “Release”) is made and entered into as of May 1, 2024, between Hilltop Holdings Inc. and any of its parents, predecessors, successors, subsidiaries, affiliates or related companies, organizations, managers, officers, directors, executives, agents, plan fiduciaries, shareholders, attorneys and/or representativ

May 3, 2024 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 1, 2024 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission File Nu

April 29, 2024 DEF 14A

UNITED STATES

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14

April 29, 2024 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ⌧ Filed by a Party other than the Registrant ◻ Check the appropriate box: ◻ Preliminary Proxy Statement ◻ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ◻ Defin

April 22, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2024 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Commission File Number: 1-31987 Hilltop Holdings Inc.

April 18, 2024 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 18, 2024 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission File

April 18, 2024 EX-99.1

Q1 2024 3 Investor Highlights – Notes: (1) Average Bank Loans HFI reflect consolidated loans held for investment excluding margin loans from the Broker-Dealer business. • PlainsCapital Bank generated $50.3 million in pre-tax income during Q1 2024 • B

Exhibit 99.1 Hilltop Holdings Inc. Q1 2024 Earnings Presentation April 19, 2024 Preface 2 Corporate Headquarters Additional Information 6565 Hillcrest Ave Dallas, TX 75205 Phone: 214-855-2177 www.hilltop.com Please Contact: Erik Yohe Phone: 214-525-4634 Email: [email protected] FORWARD-LOOKING STATEMENTS This presentation and statements made by representatives of Hilltop Holdings Inc. (“Hilltop” o

April 18, 2024 EX-99.1

March 31,

Exhibit 99.1 Investor Relations Contact: Erik Yohe 214-525-4634 [email protected] Hilltop Holdings Inc. Announces Financial Results for First Quarter 2024 DALLAS — (BUSINESS WIRE) April 18, 2024 — Hilltop Holdings Inc. (NYSE: HTH) (“Hilltop”) today announced financial results for the first quarter of 2024. Hilltop produced income to common stockholders of $27.7 million, or $0.42 per diluted share,

April 18, 2024 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 18, 2024 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission File

February 14, 2024 EX-97

Incentive Compensation Clawback Policy

Exhibit 97 INCENTIVE COMPENSATION CLAWBACK POLICY OVERVIEW The Board of Directors (“Board”) of Hilltop Holdings Inc.

February 14, 2024 EX-21.1

List of subsidiaries of the Registrant.

Exhibit 21.1 List of Subsidiaries of Hilltop Holdings Inc. As of February 14, 2024 Name State or Other Jurisdiction of Incorporation or Formation ARC Insurance Holdings, Inc. Delaware First Southwest Holdings LLC Delaware First Southwest Capital Investments, Inc. Delaware First Southwest Leasing Company Delaware FSC Asset Administrator, LLC Delaware Highland HomeLoans, LLC Delaware Hilltop Investm

February 14, 2024 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended: December 31, 2023 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 1-31987 Hilltop Hol

February 13, 2024 SC 13G/A

HTH / Hilltop Holdings Inc. / VANGUARD GROUP INC - SCHEDULE 13G/A Passive Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 (Amendment No.: 8)* Name of issuer: Hilltop Holdings Inc Title of Class of Securities: Common Stock CUSIP Number: 432748101 Date of Event Which Requires Filing of this Statement: December 29, 2023 Check the appropriate box to designate the rule pursuant to which this Schedule is filed:

February 9, 2024 SC 13G/A

HTH / Hilltop Holdings Inc. / DIMENSIONAL FUND ADVISORS LP - SEC SCHEDULE 13G Passive Investment

SC 13G/A 1 SEC13GFiling.htm SEC SCHEDULE 13G UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 1 )* Hilltop Holdings Inc (Name of Issuer) Common Stock (Title of Class of Securities) 432748101 (CUSIP Number) December 29, 2023 (Date of Event Which Requires Filing of this Statement) Check the appropriate box t

January 25, 2024 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 25, 2024 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission Fi

January 25, 2024 EX-99.1

Q4 2023 3 Investor Highlights – Notes: (1) Average Bank Loans HFI reflect consolidated loans held for investment excluding margin loans from the broker-dealer business. • PlainsCapital Bank generated $47.8 million in pre-tax income during Q4 2023 • B

Exhibit 99.1 Hilltop Holdings Inc. Q4 2023Earnings Presentation January 26, 2024 Preface 2 Corporate Headquarters Additional Information 6565 Hillcrest Ave Dallas, TX 75205 Phone: 214-855-2177 www.hilltop-holdings.com Please Contact: Erik Yohe Phone: 214-525-4634 Email: [email protected] FORWARD-LOOKING STATEMENTS This presentation and statements made by representatives of Hilltop Holding

January 25, 2024 EX-99.1

December 31,

Exhibit 99.1 Investor Relations Contact: Erik Yohe 214-525-4634 [email protected] Hilltop Holdings Inc. Announces Financial Results for Fourth Quarter and Full Year 2023 DALLAS — (BUSINESS WIRE) January 25, 2024 — Hilltop Holdings Inc. (NYSE: HTH) (“Hilltop”) today announced financial results for the fourth quarter and full year 2023. Hilltop produced income to common stockholders of $28.

January 25, 2024 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 25, 2024 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission Fi

January 10, 2024 CORRESP

United States Securities and Exchange Commission

Hilltop Holdings Inc. 6565 Hillcrest Avenue Dallas, Texas 75205 Tel: 214.855.2177 Fax: 214.855.2173 www.hilltop-holdings.com NYSE: HTH January 10, 2024 Via EDGAR United States Securities and Exchange Commission Division of Corporate Finance Mail Stop 4720 100 F Street, N.E. Washington, D.C. 20549 Attn: Jee Yeon Ahn and Lory Empie Re: Hilltop Holdings Inc. Form 10-K for Fiscal Year Ended December 3

November 20, 2023 EX-99.1

Hilltop Holdings Inc. Announces Pending Retirement of PlainsCapital Bank President and CEO Jerry Schaffner in May 2024 COO Brian Heflin Promoted to President of PlainsCapital Bank, CAO Pete Villarreal Promoted to COO, and Hilltop President and CEO Je

EXHIBIT 99.1 Hilltop Holdings Inc. Announces Pending Retirement of PlainsCapital Bank President and CEO Jerry Schaffner in May 2024 COO Brian Heflin Promoted to President of PlainsCapital Bank, CAO Pete Villarreal Promoted to COO, and Hilltop President and CEO Jeremy B. Ford to Serve as CEO DALLAS — (BUSINESS WIRE) November 20, 2023 — Hilltop Holdings Inc. (NYSE: HTH) (“Hilltop”) today announced t

November 20, 2023 8-K

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 15, 2023 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission F

October 25, 2023 EX-3.1

Fourth Amended and Restated Bylaws of Hilltop Holdings Inc. (filed as Exhibit 3.1 to the Registrant’s Current Report on Form 8-K filed on October 25, 2023 (File No. 001-31987) and incorporated herein by reference).

Exhibit 3.1 HILLTOP HOLDINGS INC. FOURTH AMENDED AND RESTATED BYLAWS Article I OFFICES Section 1. PRINCIPAL OFFICE. The principal office of the Corporation in the State of Maryland shall be located at such place as the Board of Directors may designate. Section 2. ADDITIONAL OFFICES. The Corporation may have additional offices, including a principal executive office, at such places as the Board of

October 25, 2023 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): October 19, 2023 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission Fi

October 23, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2023 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Commission File Number: 1-31987 Hilltop Holdings Inc.

October 19, 2023 EX-99.1

Q3 2023 3 Investor Highlights – Notes: (1) Average Bank Loans HFI reflect consolidated loans held for investment excluding margin loans from the broker-dealer business. • PlainsCapital Bank generated $53.2 million in pre-tax income during Q3 2023, a

Exhibit 99.1 Hilltop Holdings Inc. Q3 2023 Earnings Presentation October 20, 2023 Preface 2 Corporate Headquarters Additional Information 6565 Hillcrest Ave Dallas, TX 75205 Phone: 214-855-2177 www.hilltop-holdings.com Please Contact: Erik Yohe Phone: 214-525-4634 Email: [email protected] FORWARD-LOOKING STATEMENTS This presentation and statements made by representatives of Hilltop Holdin

October 19, 2023 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): October 19, 2023 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission Fi

October 19, 2023 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): October 19, 2023 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission Fi

October 19, 2023 EX-99.1

September 30,

Exhibit 99.1 Investor Relations Contact: Erik Yohe 214-525-4634 [email protected] Hilltop Holdings Inc. Announces Financial Results for Third Quarter 2023 DALLAS — (BUSINESS WIRE) October 19, 2023 — Hilltop Holdings Inc. (NYSE: HTH) (“Hilltop”) today announced financial results for the third quarter of 2023. Hilltop produced income to common stockholders of $37.0 million, or $0.57 per dil

July 24, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 10-Q

Table of Contents HOW UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2023 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Commission File Number: 1-31987 Hilltop Holdings Inc.

July 24, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 20, 2023 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission File

July 20, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 20, 2023 Hilltop Holdings In

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 20, 2023 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission File

July 20, 2023 EX-99.1

Q2 2023 3 Investor Highlights – Notes: (1) Average Bank Loans HFI reflect consolidated loans held for investment excluding margin loans from the broker-dealer business. (2) Mortgage Bankers Association Forecast, June 20, 2023. • PlainsCapital Bank ge

Exhibit 99.1 Hilltop Holdings Inc. Q2 2023Earnings Presentation July 21, 2023 Preface 2 Corporate Headquarters Additional Information 6565 Hillcrest Ave Dallas, TX 75205 Phone: 214-855-2177 www.hilltop-holdings.com Please Contact: Erik Yohe Phone: 214-525-4634 Email: [email protected] FORWARD-LOOKING STATEMENTS This presentation and statements made by representatives of Hilltop Holdings I

July 20, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 20, 2023 Hilltop Holdings In

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 20, 2023 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission File

July 20, 2023 EX-99.1

June 30,

Exhibit 99.1 Investor Relations Contact: Erik Yohe 214-525-4634 [email protected] Hilltop Holdings Inc. Announces Financial Results for Second Quarter 2023 DALLAS — (BUSINESS WIRE) July 20, 2023 — Hilltop Holdings Inc. (NYSE: HTH) (“Hilltop”) today announced financial results for the second quarter of 2023. Hilltop produced income to common stockholders of $18.1 million, or $0.28 per dilu

July 3, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 3, 2023 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission File N

April 28, 2023 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ⌧ Filed by a Party other than the Registrant ◻ Check the appropriate box: ◻ Preliminary Proxy Statement ◻ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ◻ Defin

April 28, 2023 DEF 14A

UNITED STATES

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14

April 26, 2023 10-Q/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 10-Q/A (Amendment No. 1)

Table of Contents HOW UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 10-Q/A (Amendment No.

April 24, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 10-Q

Table of Contents HOW UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2023 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Commission File Number: 1-31987 Hilltop Holdings Inc.

April 20, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 20, 2023 Hilltop Holdings I

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 20, 2023 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission File

April 20, 2023 EX-99.1

Q1 2023 3 Investor Highlights – Notes: (1) Average Bank Loans HFI reflect consolidated loans held for investment excluding margin loans from the broker-dealer business. (2) Mortgage Bankers Association Forecast, March 20, 2023. • PlainsCapital Bank g

Exhibit 99.1 Hilltop Holdings Inc. Q1 2023 Earnings Presentation April 21, 2023 Preface 2 Corporate Headquarters Additional Information 6565 Hillcrest Ave Dallas, TX 75205 Phone: 214-855-2177 www.hilltop-holdings.com Please Contact: Erik Yohe Phone: 214-525-4634 Email: [email protected] FORWARD-LOOKING STATEMENTS This presentation and statements made by representatives of Hilltop Holdings

April 20, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 20, 2023 Hilltop Holdings I

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 20, 2023 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission File

April 20, 2023 EX-99.1

March 31,

Exhibit 99.1 Investor Relations Contact: Erik Yohe 214-525-4634 [email protected] Hilltop Holdings Inc. Announces Financial Results for First Quarter 2023 DALLAS — (BUSINESS WIRE) April 20, 2023 — Hilltop Holdings Inc. (NYSE: HTH) (“Hilltop”) today announced financial results for the first quarter 2023. Hilltop produced income to common stockholders of $25.8 million, or $0.40 per diluted

February 17, 2023 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended: December 31, 2022 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 1-31987 Hilltop Hol

February 17, 2023 EX-21.1

List of subsidiaries of the Registrant.

Exhibit 21.1 List of Subsidiaries of Hilltop Holdings Inc. As of February 17, 2023 Name State or Other Jurisdiction of Incorporation or Formation ARC Insurance Holdings, Inc. Delaware Ariva Mortgage Services, LLC Delaware First Southwest Holdings LLC Delaware First Southwest Capital Investments, Inc. Delaware First Southwest Leasing Company Delaware FSC Asset Administrator, LLC Delaware Grand Home

February 10, 2023 SC 13G

HTH / Hilltop Holdings Inc. / DIMENSIONAL FUND ADVISORS LP - SEC SCHEDULE 13G Passive Investment

SC 13G 1 SEC13GFiling.htm SEC SCHEDULE 13G UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* Hilltop Holdings Inc (Name of Issuer) Common Stock (Title of Class of Securities) 432748101 (CUSIP Number) December 30, 2022 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to de

February 9, 2023 SC 13G/A

HTH / Hilltop Holdings Inc. / VANGUARD GROUP INC - SCHEDULE 13G/A Passive Investment

SC 13G/A 1 tv01083-hilltopholdingsinc.htm SCHEDULE 13G/A SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 (Amendment No.: 7)* Name of issuer: Hilltop Holdings Inc. Title of Class of Securities: Common Stock CUSIP Number: 432748101 Date of Event Which Requires Filing of this Statement: December 30, 2022 Check the appropriate box to des

January 26, 2023 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 26, 2023 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission Fi

January 26, 2023 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 26, 2023 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission Fi

January 26, 2023 EX-99.1

December 31,

Exhibit 99.1 Investor Relations Contact: Erik Yohe 214-525-4634 [email protected] Hilltop Holdings Inc. Announces Financial Results for Fourth Quarter and Full Year 2022 DALLAS — (BUSINESS WIRE) January 26, 2023 — Hilltop Holdings Inc. (NYSE: HTH) (“Hilltop”) today announced financial results for the fourth quarter and full year 2022. Hilltop produced income to common stockholders of $25.

January 26, 2023 EX-99.1

Q4 2022 3Investor Highlights –Notes:(1)Average Bank Loans HFI reflect consolidated loans held for investment excluding margin loans from the broker-dealer business. •PlainsCapital Bank generated $58.0 million in pre-tax income during Q4 2022 relative

Exhibit 99.1 Hilltop Holdings Inc.Earnings PresentationQ4 2022 January 27, 2023 Preface 2 Additional Information Corporate Headquarters6565 Hillcrest AveDallas, TX 75205Phone: 214-855-2177www.hilltop-holdings.com Please Contact:Erik YohePhone: 214-525-4634Email: [email protected] STATEMENTSThis presentation and statements made by representatives of Hilltop Holdings Inc. (“H

January 4, 2023 EX-10.8(2)

First Amendment to Employment Agreement by and between Hilltop Holdings Inc. and Steve Thompson, dated as of December 30, 2022 (filed as Exhibit 10.8.2 to the Registrant’s Current Report on Form 8-K filed January 4, 2023 (File No. 001-31987) and incorporated herein by reference).

EX-10.8(2) 2 tm231539d1ex10d8-2.htm EXHIBIT 10.8.2 EXHIBIT 10.8.2 FIRST AMENDMENT TO EMPLOYMENT AGREEMENT THIS FIRST AMENDMENT TO EMPLOYMENT AGREEMENT (this “Amendment”) is made and entered into as of December 30, 2022 (the “Execution Date”), by and between Hilltop Holdings Inc. (the “Company”), on behalf of itself and all of its subsidiaries (collectively, “Employer”), and Steve Thompson (“Execut

January 4, 2023 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): December 30, 2022 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission F

October 24, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 10-Q

Table of Contents HOW ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 ? FORM 10-Q ? ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 ? For the quarterly period ended September 30, 2022 ? ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 ? Commission File Number: 1-31987 ? Hilltop Holdings Inc.

October 20, 2022 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 ? FORM 8-K ? CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 ? Date of Report (Date of earliest event reported): October 20, 2022 ? Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) ? ? ? ? ? ? Maryland ? 1-31987 ? 84-1477939 (State or other jurisdiction of incor

October 20, 2022 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 ? FORM 8-K ? CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 ? Date of Report (Date of earliest event reported): October 20, 2022 ? Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) ? ? ? ? ? ? Maryland ? 1-31987 ? 84-1477939 (State or other jurisdiction of incor

October 20, 2022 EX-99.1

Q3 2022 3Investor Highlights –Notes:(1)Average Bank Loans HFI reflect consolidated loans held for investment excluding margin loans from the broker-dealer business.(2)Mortgage Bankers Association Forecast, September 19, 2022. •PlainsCapital Bank gene

Exhibit 99.1 Hilltop Holdings Inc.Earnings PresentationQ3 2022 October 21, 2022 Preface 2 Additional Information Corporate Headquarters6565 Hillcrest AveDallas, TX 75205Phone: 214-855-2177www.hilltop-holdings.com Please Contact:Erik YohePhone: 214-525-4634Email: [email protected] STATEMENTSThis presentation and statements made by representatives of Hilltop Holdings Inc. (?H

October 20, 2022 EX-99.1

September 30,

Exhibit 99.1 ? ? Investor Relations Contact: ? Erik Yohe ? 214-525-4634 ? [email protected] ? Hilltop Holdings Inc. Announces Financial Results for Third Quarter 2022 ? DALLAS ? (BUSINESS WIRE) October 20, 2022 ? Hilltop Holdings Inc. (NYSE: HTH) (?Hilltop?) today announced financial results for the third quarter of 2022. Hilltop produced income to common stockholders of $32.1 million, or

September 9, 2022 SC 13D/A

HTH / Hilltop Holdings Inc. / Ford Gerald J - SC 13D/A Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 16)* HILLTOP HOLDINGS INC. (Name of Issuer) Common Stock, par value $0.01 per share (Title of Class of Securities) 432748 10 1 (CUSIP Number) Corey G. Prestidge 6565 Hillcrest Avenue Dallas, Texas 75205 (214) 525-4647 (Name, Address and Telephone Number of P

August 31, 2022 EX-10.7(3)

Second Amendment to Employment Agreement by and between Hilltop Holdings Inc. and William B. Furr dated as of August 20, 2022 (filed as Exhibit 10.7.3 to the Registrant’s Current Report as Form 8-K filed August 31, 2022 (file No. 009-31987) and incorporated by reference).

Exhibit 10.7.3 SECOND AMENDMENT TO EMPLOYMENT AGREEMENT THIS SECOND AMENDMENT TO EMPLOYMENT AGREEMENT (this ?Amendment?) is made and entered into as of August 30, 2022 (the ?Execution Date?), by and between Hilltop Holdings Inc. (?Company?), on behalf of itself and all of its subsidiaries (collectively, ?Employer?), and William B. Furr (?Executive?). Each initially capitalized term used, but not o

August 31, 2022 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 30, 2022 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission Fil

August 8, 2022 S-8

As filed with the Securities and Exchange Commission on August 8, 2022

As filed with the Securities and Exchange Commission on August 8, 2022 Registration No.

August 8, 2022 EX-FILING FEES

Filing Fee Table.

Exhibit 107 CALCULATION OF FILING FEE TABLE Form S-8 (Form Type) Hilltop Holdings Inc.

July 25, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 10-Q

Table of Contents HOW ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 ? FORM 10-Q ? ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 ? For the quarterly period ended June 30, 2022 ? ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 ? Commission File Number: 1-31987 ? Hilltop Holdings Inc.

July 22, 2022 EX-10.1

First Amendment to Hilltop Holdings Inc Employee Stock Purchase Plan (filed as Exhibit 10.1 to the Registrant’s Current Report on Form 8-K filed July 22, 2022 (File No. 001-31987) and incorporated herein by reference).

Exhibit 10.1 FIRST AMENDMENT TO Hilltop Holdings Inc. EMPLOYEE STOCK PURCHASE PLAN This FIRST AMENDMENT TO Hilltop Holdings Inc. EMPLOYEE STOCK PURCHSE Plan (this ?Amendment?), effective as of April 21, 2022 (the ?Effective Date?), is made and entered into by Hilltop Holdings Inc., a Maryland corporation (the ?Company?). Terms used in this Amendment with initial capital letters that are not otherw

July 22, 2022 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Submission of Matters to a Vote of Security Holders, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 21, 2022 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission File

July 21, 2022 EX-99.1

June 30,

Exhibit 99.1 ? ? Investor Relations Contact: ? Erik Yohe ? 214-525-4634 ? [email protected] ? Hilltop Holdings Inc. Announces Financial Results for Second Quarter 2022 ? DALLAS ? (BUSINESS WIRE) July 21, 2022 ? Hilltop Holdings Inc. (NYSE: HTH) (?Hilltop?) today announced financial results for the second quarter of 2022. Hilltop produced income to common stockholders of $33.3 million, or

July 21, 2022 EX-99.1

Q2 2022 3Investor Highlights –Notes:(1)Bank Loans HFI reflect consolidated loans held for investment excluding margin loans from the broker-dealer business.(2)Mortgage Bankers Association Forecast, July 18, 2022. •PlainsCapital Bank generated $51.4 m

Exhibit 99.1 Hilltop Holdings Inc.Earnings PresentationQ2 2022 July 22, 2022 Preface 2 Additional Information Corporate Headquarters6565 Hillcrest AveDallas, TX 75205Phone: 214-855-2177www.hilltop-holdings.com Please Contact:Erik YohePhone: 214-525-4634Email: [email protected] STATEMENTSThis presentation and statements made by representatives of Hilltop Holdings Inc. (?Hill

July 21, 2022 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 ? FORM 8-K ? CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 ? Date of Report (Date of earliest event reported): July 21, 2022 ? Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) ? ? ? ? ? ? Maryland ? 1-31987 ? 84-1477939 (State or other jurisdiction of incorpor

July 21, 2022 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 ? FORM 8-K ? CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 ? Date of Report (Date of earliest event reported): July 21, 2022 ? Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) ? ? ? ? ? ? Maryland ? 1-31987 ? 84-1477939 (State or other jurisdiction of incorpor

July 13, 2022 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant x Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Defin

July 13, 2022 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant x Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Defin

June 3, 2022 SC 13G

HTH / Hilltop Holdings Inc. / MILLENNIUM MANAGEMENT LLC Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 HILLTOP HOLDINGS INC. (Name of Issuer) COMMON STOCK, PAR VALUE $0.01 PER SHARE (Title of Class of Securities) 432748101 (CUSIP Number) MAY 26, 2022 (Date of event which requires filing of this statement) Check the appropriate box to designate the rule pursuant to which thi

June 2, 2022 EX-99.(A)(5)(III)

Press release announcing final results of the tender offer, dated June 2, 2022.

Exhibit (a)(5)(iii) Media Contact: Ben Brooks 214-252-4047 [email protected] Investor Relations Contact: Erik Yohe 214-525-4634 [email protected] Hilltop Holdings Inc. Announces Final Results of Tender Offer DALLAS (June 2, 2022) ? Hilltop Holdings Inc. (NYSE: HTH) (?Hilltop? or the ?Company?) announced today the final results of its modified ?Dutch auction? tender offer to

June 2, 2022 SC TO-I/A

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO (Amendment No. 2) Tender Offer Statement under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act of 1934 Hilltop Holdings Inc. (Name of Subject Company (Issuer)) Hilltop

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO (Amendment No. 2) Tender Offer Statement under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act of 1934 Hilltop Holdings Inc. (Name of Subject Company (Issuer)) Hilltop Holdings Inc. (Names of filing Persons (Offeror and Issuer)) Common Stock, Par Value $0.01 per share (Title of Class of Securities) 432748101 (CUSIP N

June 2, 2022 EX-FILING FEES

Filing Fee Table.

Exhibit 107 PRIVILEGED AND CONFIDENTIAL Calculation of Filing Fee Tables SC TO-I (Form Type) Hilltop Holdings Inc.

May 31, 2022 EX-99.(A)(5)(II)

Press release announcing preliminary results of the tender offer, dated May 31, 2022.

Exhibit (a)(5)(ii) Media Contact: Ben Brooks 214-252-4047 [email protected] Investor Relations Contact: Erik Yohe 214-525-4634 [email protected] Hilltop Holdings Inc. Announces Preliminary Results of Tender Offer DALLAS (May 31, 2022) ? Hilltop Holdings Inc. (NYSE: HTH) (?Hilltop? or the ?Company?) announced today the preliminary results of its modified ?Dutch auction? tende

May 31, 2022 SC TO-I/A

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO (Amendment No. 1) Tender Offer Statement under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act of 1934 Hilltop Holdings Inc. (Name of Subject Company (Issuer)) Hilltop

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO (Amendment No. 1) Tender Offer Statement under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act of 1934 Hilltop Holdings Inc. (Name of Subject Company (Issuer)) Hilltop Holdings Inc. (Names of filing Persons (Offeror and Issuer)) Common Stock, Par Value $0.01 per share (Title of Class of Securities) 432748101 (CUSIP N

May 2, 2022 DEF 14A

Definitive Proxy Statement on Schedule 14A for the 2022 Annual Meeting, filed with the Securities and Exchange Commission on May 2, 2022,

Table of Contents ? ? ? ? ? ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

May 2, 2022 EX-99.(A)(1)(II)

Form of Letter of Transmittal.

? ?Exhibit (a)(1)(ii)? LETTER OF TRANSMITTAL To Tender Shares of Common Stock Pursuant to the Offer to Purchase Dated May 2, 2022 by HILLTOP HOLDINGS INC.

May 2, 2022 EX-99.(A)(1)(V)

Letter to clients for use by brokers, dealers, commercial banks, trust companies and other nominees, dated May 2, 2022.

? ?Exhibit (a)(1)(v)? Offer by HILLTOP HOLDINGS INC. to Purchase for Cash Up to $400,000,000 of its Common Stock At a Purchase Price Not Less Than $28.00 Per Share and Not More Than $32.00 Per Share ? ? THE TENDER OFFER, THE PRORATION PERIOD AND WITHDRAWAL RIGHTS EXPIRE AT 12:00 MIDNIGHT, NEW YORK CITY TIME, AT THE END OF THE DAY ON MAY 27, 2022, UNLESS THE TENDER OFFER IS EXTENDED OR TERMINATED.

May 2, 2022 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ? Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Defin

May 2, 2022 SC TO-I

As filed with the Securities and Exchange Commission on May 2, 2022 SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO Tender Offer Statement under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act of 1934 Hilltop Holding

? As filed with the Securities and Exchange Commission on May 2, 2022 ? ? SECURITIES AND EXCHANGE COMMISSION Washington, D.

May 2, 2022 EX-99.(A)(1)(I)

Offer to Purchase, dated May 2, 2022.

TABLE OF CONTENTS ?Exhibit (a)(1)(i)? HILLTOP HOLDINGS INC. Offer to Purchase for Cash Up to $400,000,000 of its Common Stock At a Purchase Price Not Less Than $28.00 Per Share and Not More Than $32.00 Per Share CUSIP: 432748101 ? ? THE TENDER OFFER, THE PRORATION PERIOD AND WITHDRAWAL RIGHTS EXPIRE AT 12:00 MIDNIGHT, NEW YORK CITY TIME, AT THE END OF THE DAY ON MAY 27, 2022, UNLESS THE TENDER OFF

May 2, 2022 EX-FILING FEES

Filing Fee Table.

Exhibit 107 Calculation of Filing Fee Tables SC TO-I (Form Type) Hilltop Holdings Inc.

May 2, 2022 EX-99.(A)(1)(IV)

Letter to brokers, dealers, commercial banks, trust companies and other nominees, dated May 2, 2022.

? ?Exhibit (a)(1)(iv)? Offer by HILLTOP HOLDINGS INC. to Purchase for Cash Up to $400,000,000 of its Common Stock At a Purchase Price Not Less Than $28.00 Per Share and Not More Than $32.00 Per Share ? ? THE TENDER OFFER, THE PRORATION PERIOD AND WITHDRAWAL RIGHTS EXPIRE AT 12:00 MIDNIGHT, NEW YORK CITY TIME, AT THE END OF THE DAY ON MAY 27, 2022, UNLESS THE TENDER OFFER IS EXTENDED OR TERMINATED.

May 2, 2022 EX-99.(A)(5)(I)

Press release announcing the tender offer, dated May 2, 2022.

? ?Exhibit (a)(5)(i)? Media Contact: Ben Brooks 214-252-4047 [email protected] Investor Relations Contact: Erik Yohe 214-525-4634 [email protected] Hilltop Holdings Inc. Commences a Modified Dutch Auction Tender Offer to Repurchase up to $400 Million of its Common Stock DALLAS (May 2, 2022)???Hilltop Holdings Inc. (NYSE: HTH) (?Hilltop? or the ?Company?) announced today that

May 2, 2022 EX-99.(A)(1)(III)

Notice of Guaranteed Delivery.

? ?Exhibit (a)(1)(iii)? NOTICE OF GUARANTEED DELIVERY (Not to Be Used For Signature Guarantee) To Tender Shares of Common Stock Pursuant to the Offer to Purchase Dated May 2, 2022 by HILLTOP HOLDINGS INC.

May 2, 2022 EX-99.(A)(1)(VI)

Summary Advertisement, dated May 2, 2022.

? ?Exhibit (a)(1)(vi)? This announcement is neither an offer to purchase nor a solicitation of an offer to sell shares of Hilltop Holdings Inc.

April 25, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 10-Q

Table of Contents HOW ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 ? FORM 10-Q ? ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 ? For the quarterly period ended March 31, 2022 ? ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 ? Commission File Number: 1-31987 ? Hilltop Holdings Inc.

April 21, 2022 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 ? FORM 8-K ? CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 ? Date of Report (Date of earliest event reported): April 21, 2022 ? Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) ? ? ? ? ? ? Maryland ? 1-31987 ? 84-1477939 (State or other jurisdiction of incorpo

April 21, 2022 EX-99.1

March 31,

Exhibit 99.1 ? ? Investor Relations Contact: ? Erik Yohe ? 214-525-4634 ? [email protected] ? Hilltop Holdings Inc. Announces Financial Results for First Quarter 2022 ? DALLAS ? (BUSINESS WIRE) April 21, 2022 ? Hilltop Holdings Inc. (NYSE: HTH) (?Hilltop?) today announced financial results for the first quarter of 2022. Hilltop produced income to common stockholders of $22.3 million, or $

April 21, 2022 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 ? FORM 8-K ? CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 ? Date of Report (Date of earliest event reported): April 21, 2022 ? Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) ? ? ? ? ? ? Maryland ? 1-31987 ? 84-1477939 (State or other jurisdiction of incorpo

April 21, 2022 EX-99.1

Q1 2022 3 Investor Highlights – Notes: (1) Bank Loans HFI reflect consolidated loans held for investment excluding margin loans from the broker - dealer business. (2) Mortgage Bankers Association Forecast, April 13, 2022. • PlainsCapital Bank generat

Exhibit 99.1 Hilltop Holdings Inc. Earnings Presentation Q1 2022 April 22, 2022 Preface 2 Additional Information Corporate Headquarters 6565 Hillcrest Ave Dallas, TX 75205 Phone: 214 - 855 - 2177 www.hilltop - holdings.com Please Contact: Erik Yohe Phone: 214 - 525 - 4634 Email: eyohe@hilltop - holdings.com FORWARD - LOOKING STATEMENTS This presentation and statements made by representatives of Hi

April 5, 2022 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): March 31, 2022 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission File

April 5, 2022 EX-10.7(2)

First Amendment to Employment Agreement by and between Hilltop Holdings Inc. and Martin B. Winges, dated as of March 31, 2022, but effective as of February 19, 2022 (filed as Exhibit 10.7.2 to the Registrant’s Current Report on Form 8-K filed on April 4, 2022 (File No. 001-31987) and incorporated herein by reference).

EXHIBIT 10.7.2 FIRST AMENDMENT TO EMPLOYMENT AGREEMENT THIS FIRST AMENDMENT TO EMPLOYMENT AGREEMENT (this ?Amendment?) is made and entered into as of March 31, 2022 (the ?Execution Date?), but effective as of February 19, 2022, by and between Hilltop Holdings Inc. (the ?Company?), on behalf of itself and all of its subsidiaries (collectively, ?Employer?), and Martin B. Winges (?Executive?). Each i

February 15, 2022 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

Table of Contents ? ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

February 15, 2022 EX-10.13.1

First Amendment to Retail Lease between SPC Park Plaza Partners, LLC, Diamond Hillcrest, LLC, and HTH Hillcrest Project LLC, as Co-Owners, and PlainsCapital Bank, as Tenant, dated as of December 16, 2021, but effective as of August 1, 2019 (filed as Exhibit 10.13.1 to the Registrant’s Annual Report on Form 10-K for the year ended December 31, 2021 filed on February 15, 2022 (File No. 001-31987) and incorporated herein by reference).

EXHIBIT 10.13.1 ? FIRST AMENDMENT TO RETAIL LEASE This First Amendment to Retail Lease (this "Amendment") is made and entered as of the 16th day of December 2021, but effective as of August 1, 2019 (the "Effective Date"), by and between SPC PARK PLAZA PARTNERS LLC, a Texas limited liability company, DIAMOND HILLCREST, LLC, a Texas limited liability company, and HTH HILLCREST PROJECT, LLC, a Texas

February 15, 2022 EX-10.11.1

First Amendment to Hilltop Plaza Co-Owners Agreement, by and among Diamond Hillcrest, LLC, HTH Hillcrest Project LLC and SPC Park Plaza Partners, LLC, dated as of December 31, 2021 (filed as Exhibit 10.11.1 to the Registrant’s Annual Report on Form 10-K for the year ended December 31, 2021 filed on February 15, 2022 (File No. 001-31987) and incorporated herein by reference.

EXHIBIT 10.11.1 FIRST AMENDMENT TO CO-Owners AGREEMENT ? THIS FIRST AMENDMENT TO THE CO-OWNERS AGREEMENT ("First Amendment") is entered into to be effective as of the 31st day of December 2021 (the "First Amendment Effective Date"), by and among Diamond Hillcrest, LLC, a Texas limited liability company ("Ford Owner"), HTH Hillcrest Project LLC, a Texas limited liability company ("Hilltop Owner"),

February 15, 2022 EX-10.12.1

First Amendment to Office Lease between SPC Park Plaza Partners, LLC, Diamond Hillcrest, LLC, and HTH Hillcrest Project LLC, as Co-Owners, and Hilltop Holdings Inc., as Tenant, dated as of November 30, 2021, but effective as of June 29, 2019 (filed as Exhibit 10.12.1 to the Registrant’s Annual Report on Form 10-K for the year ended December 31, 2021 filed on February 15, 2022 (File No. 001-31987) and incorporated herein by reference)

EXHIBIT 10.12.1 FIRST AMENDMENT TO OFFICE LEASE ? This First Amendment to Office Lease (this ?Amendment?) is made and entered into as of the 30th day of November 2021, but effective as of June 29, 2019 (the ?Effective Date?) by and among SPC PARK PLAZA PARTNERS LLC, a Texas limited liability company (?SPC?), DIAMOND HILLCREST, LLC, a Texas limited liability company (?Diamond?), HTH HILLCREST PROJE

February 15, 2022 EX-21.1

List of subsidiaries of the Registrant.

Exhibit 21.1 ? List of Subsidiaries of Hilltop Holdings Inc. As of February 15, 2022 ? ? ? ? Name State or Other Jurisdiction of Incorporation or Formation ARC Insurance Holdings, Inc. ? Delaware Ariva Mortgage Services, LLC ? Delaware First Southwest Holdings LLC ? Delaware First Southwest Capital Investments, Inc. ? Delaware First Southwest Leasing Company ? Delaware FSC Asset Administrator, LLC

February 10, 2022 SC 13G/A

HTH / Hilltop Holdings Inc. / VANGUARD GROUP INC - SCHEDULE 13G/A Passive Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 (Amendment No.: 6)* Name of issuer: Hilltop Holdings Inc. Title of Class of Securities: Common Stock CUSIP Number: 432748101 Date of Event Which Requires Filing of this Statement: December 31, 2021 Check the appropriate box to designate the rule pursuant to which this Schedule is filed:

February 8, 2022 SC 13G/A

HTH / Hilltop Holdings Inc. / DIMENSIONAL FUND ADVISORS LP - SEC SCHEDULE 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 5 )* Hilltop Holdings Inc (Name of Issuer) Common Stock (Title of Class of Securities) 432748101 (CUSIP Number) December 31, 2021 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which this S

January 27, 2022 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 ? FORM 8-K ? CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 ? Date of Report (Date of earliest event reported): January 27, 2022 ? Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) ? ? ? ? ? ? Maryland ? 1-31987 ? 84-1477939 (State or other jurisdiction of incor

January 27, 2022 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 27, 2022 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission Fi

January 27, 2022 EX-99.1

December 31,

Exhibit 99.1 ? ? Investor Relations Contact: ? Erik Yohe ? 214-525-4634 ? [email protected] ? Hilltop Holdings Inc. Announces Financial Results for Fourth Quarter and Full Year 2021 ? DALLAS ? (BUSINESS WIRE) January 27, 2022 ? Hilltop Holdings Inc. (NYSE: HTH) (?Hilltop?) today announced financial results for the fourth quarter and full year 2021. Hilltop produced income from continuing

January 27, 2022 EX-99.1

Hilltop Holdings Inc. Earnings Presentation Q4 2021 January 28, 2022 Q4 2021 3 Investor Highlights – Notes: (1) Average Bank Loans HFI reflect consolidated loans held for investment excluding margin loans from the broker - dealer business. (2) Mortga

Exhibit 99.1 Hilltop Holdings Inc. Earnings Presentation Q4 2021 January 28, 2022 Preface 2 Additional Information Corporate Headquarters 6565 Hillcrest Ave Dallas, TX 75205 Phone: 214 - 855 - 2177 www.hilltop - holdings.com Please Contact: Erik Yohe Phone: 214 - 525 - 4634 Email: eyohe@hilltop - holdings.com FORWARD - LOOKING STATEMENTS This presentation and statements made by representatives of

October 29, 2021 8-K/A

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 ? FORM 8-K/A ? AMENDMENT NO. 1 ? CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 ? Date of Report (Date of earliest event reported): October 28, 2021 ? Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) ? ? ? ? ? ? Maryland ? 1-31987 ? 84-1477939 (State or other j

October 29, 2021 EX-99.1

Hilltop Holdings Inc. Earnings Presentation Q3 2021 October 29, 2021 Q3 2021 3 Investor Highlights – Notes: (1) Average Bank Loans HFI reflect consolidated loans held for investment excluding margin loans from the broker-dealer business. • • PlainsCa

Exhibit 99.1 Hilltop Holdings Inc. Earnings Presentation Q3 2021 October 29, 2021 Preface 2 Additional Information Corporate Headquarters 6565 Hillcrest Ave Dallas, TX 75205 Phone: 214-855-2177 www.hilltop-holdings.com Please Contact: Erik Yohe Phone: 214-525-4634 Email: [email protected] FORWARD-LOOKING STATEMENTS This presentation and statements made by representatives of Hilltop Holdin

October 28, 2021 EX-99.1

September 30,

Exhibit 99.1 ? ? Investor Relations Contact: ? Erik Yohe ? 214-525-4634 ? [email protected] ? Hilltop Holdings Inc. Announces Financial Results for Third Quarter 2021 ? DALLAS ? (BUSINESS WIRE) October 28, 2021 ? Hilltop Holdings Inc. (NYSE: HTH) (?Hilltop?) today announced financial results for the third quarter of 2021. Hilltop produced income from continuing operations to common stockh

October 28, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 ? FORM 8-K ? CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 ? Date of Report (Date of earliest event reported): October 28, 2021 ? Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) ? ? ? ? ? ? Maryland ? 1-31987 ? 84-1477939 (State or other jurisdiction of incor

October 28, 2021 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 10-Q

Table of Contents ? ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 ? FORM 10-Q ? ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 ? For the quarterly period ended September 30, 2021 ? ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 ? Commission File Number: 1-31987 ? Hilltop Holdings Inc.

October 28, 2021 EX-99.1

Hilltop Holdings Inc. Earnings Presentation Q3 2021 October 29, 2021 Q3 2021 3 Investor Highlights – Notes: (1) Average Bank Loans HFI reflect consolidated loans held for investment excluding margin loans from the broker-dealer business. • PlainsCapi

EX-99.1 2 hth-20211028xex99d1.htm EX-99.1 Exhibit 99.1 Hilltop Holdings Inc. Earnings Presentation Q3 2021 October 29, 2021 Preface 2 Additional Information Corporate Headquarters 6565 Hillcrest Ave Dallas, TX 75205 Phone: 214-855-2177 www.hilltop-holdings.com Please Contact: Erik Yohe Phone: 214-525-4634 Email: [email protected] FORWARD-LOOKING STATEMENTS This presentation and statements

October 28, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 ? FORM 8-K ? CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 ? Date of Report (Date of earliest event reported): October 28, 2021 ? Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) ? ? ? ? ? ? Maryland ? 1-31987 ? 84-1477939 (State or other jurisdiction of incor

July 26, 2021 8-K

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 22, 2021 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission File

July 26, 2021 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 10-Q

Table of Contents ? ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 ? FORM 10-Q ? ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 ? For the quarterly period ended June 30, 2021 ? ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 ? Commission File Number: 1-31987 ? Hilltop Holdings Inc.

July 22, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 ? FORM 8-K ? CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 ? Date of Report (Date of earliest event reported): July 22, 2021 ? Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) ? ? ? ? ? ? Maryland ? 1-31987 ? 84-1477939 (State or other jurisdiction of incorpor

July 22, 2021 EX-99.1

June 30,

EX-99.1 2 hth-20210722xex99d1.htm EX-99.1 Exhibit 99.1 Investor Relations Contact: Erik Yohe 214-525-4634 [email protected] Hilltop Holdings Inc. Announces Financial Results for Second Quarter 2021 DALLAS — (BUSINESS WIRE) July 22, 2021 — Hilltop Holdings Inc. (NYSE: HTH) (“Hilltop”) today announced financial results for the second quarter of 2021. Hilltop produced income from continuing

July 22, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 ? FORM 8-K ? CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 ? Date of Report (Date of earliest event reported): July 22, 2021 ? Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) ? ? ? ? ? ? Maryland ? 1-31987 ? 84-1477939 (State or other jurisdiction of incorpor

July 22, 2021 EX-99.1

Hilltop Holdings Inc. Earnings Presentation Q2 2021 July 23, 2021 Q2 2021 3 Investor Highlights – Notes: (1) Average Bank Loans HFI reflect consolidated loans held for investment excluding margin loans from the broker-dealer business. • PlainsCapital

Exhibit 99.1 Hilltop Holdings Inc. Earnings Presentation Q2 2021 July 23, 2021 Preface 2 Additional Information Corporate Headquarters 6565 Hillcrest Ave Dallas, TX 75205 Phone: 214-855-2177 www.hilltop-holdings.com Please Contact: Erik Yohe Phone: 214-525-4634 Email: [email protected] FORWARD-LOOKING STATEMENTS This presentation and statements made by representatives of Hilltop Holdings

June 24, 2021 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

DEFA14A 1 tm2120629d1defa14a.htm DEFA14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant x Filed by a Party other than the Registrant ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission Only (

April 30, 2021 DEF 14A

- DEF 14A

DEF 14A 1 tmb-20210622xdef14a.htm DEF 14A Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ⌧ Filed by a Party other than the Registrant ◻ Check the appropriate box: ◻ Preliminary Proxy Statement ◻ Confidential, for Use of th

April 30, 2021 DEFA14A

- DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ? Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Defin

April 26, 2021 10-Q

Quarterly Report - 10-Q

Table of Contents ? ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 ? FORM 10-Q ? ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 ? For the quarterly period ended March 31, 2021 ? ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 ? Commission File Number: 1-31987 ? Hilltop Holdings Inc.

April 26, 2021 EX-10.1

Compensation arrangement of Jeremy B. Ford (filed as Exhibit 10.1 to the Registrant’s Quarterly Report on Form 10-Q filed on April 23, 2021 (File No. 001-31987) and incorporated herein by reference).

Exhibit 10.1 ? Compensation of Jeremy B. Ford Until March 27, 2021 ? ? ? Annual Base Salary: $775,000 ? ? Annual Incentive Plan: Mr. Jeremy Ford is entitled to participate in the Hilltop Holdings Inc. 2012 Annual Incentive Plan, as amended. His target is 100% of Annual Base Salary. ? ? Long-Term Incentive Plan: Mr. Ford is entitled to participate in the Hilltop Holdings Inc. 2012 Annual Incentive

April 26, 2021 EX-10.2

Form of Restricted Stock Unit Award Agreement (Performance-Based) for awards beginning in 2021 (filed as Exhibit 10.2 to the Registrant’s Quarterly Report on Form 10-Q filed on April 23, 2021 (File No. 001-31987) and incorporated herein by reference).

Exhibit 10.2 ? Form of RESTRICTED STOCK UNIT AWARD AGREEMENT THIS RESTRICTED STOCK UNIT AWARD AGREEMENT (this ?Agreement?), dated as of , between Hilltop Holdings Inc., a Maryland corporation (the ?Company?), and (the ?Participant?). W I T N E S S E T H In consideration of the mutual promises and covenants made herein and the mutual benefits to be derived herefrom, the parties hereto agree as foll

April 26, 2021 EX-10.3

Form of Restricted Stock Unit Award Agreement (Time-Based Vesting for Section 16 Officers) for awards beginning in 2021 (filed as Exhibit 10.3 to the Registrant’s Quarterly Report on Form 10-Q filed on April 23, 2021 (File No. 001-31987) and incorporated herein by reference).

Exhibit 10.3 ? FORM OF RESTRICTED STOCK UNIT AWARD AGREEMENT THIS RESTRICTED STOCK UNIT AWARD AGREEMENT (this ?Agreement?), dated as of , between Hilltop Holdings Inc., a Maryland corporation (the ?Company?), and (the ?Participant?). W I T N E S S E T H In consideration of the mutual promises and covenants made herein and the mutual benefits to be derived herefrom, the parties hereto agree as foll

April 26, 2021 EX-10.4

Form of Restricted Stock Unit Award Agreement (Time-Based Vesting for Non-Section 16 Officers) for awards beginning in 2020 (filed as Exhibit 10.4 to the Registrant’s Quarterly Report on Form 10-Q filed on April 26, 2021 (File No. 001-31987) and incorporated herein by reference).

Exhibit 10.4 ? FORM OF RESTRICTED STOCK UNIT AWARD AGREEMENT THIS RESTRICTED STOCK UNIT AWARD AGREEMENT (this ?Agreement?), dated as of , between Hilltop Holdings Inc., a Maryland corporation (the ?Company?), and (the ?Participant?). W I T N E S S E T H In consideration of the mutual promises and covenants made herein and the mutual benefits to be derived herefrom, the parties hereto agree as foll

April 22, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 ? FORM 8-K ? CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 ? Date of Report (Date of earliest event reported): April 22, 2021 ? Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) ? ? ? ? ? ? Maryland ? 1-31987 ? 84-1477939 (State or other jurisdiction of incorpo

April 22, 2021 EX-99.1

March 31,

Exhibit 99.1 ? ? Investor Relations Contact: ? Erik Yohe ? 214-525-4634 ? [email protected] ? Hilltop Holdings Inc. Announces Financial Results for First Quarter 2021 ? DALLAS ? (BUSINESS WIRE) April 22, 2021 ? Hilltop Holdings Inc. (NYSE: HTH) (?Hilltop?) today announced financial results for the first quarter 2021. Hilltop produced income from continuing operations to common stockholder

April 22, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 ? FORM 8-K ? CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 ? Date of Report (Date of earliest event reported): April 22, 2021 ? Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) ? ? ? ? ? ? Maryland ? 1-31987 ? 84-1477939 (State or other jurisdiction of incorpo

April 22, 2021 EX-99.1

Hilltop Holdings Inc. Earnings Presentation Q1 2021 April 23, 2021 3 Investor Highlights – ROAA .86% EPS – Diluted $0.30 ROAE 5.76% Notes: (1) Average Bank Loans HFI reflect consolidated loans held for investment excluding margin loans from the broke

Exhibit 99.1 Hilltop Holdings Inc. Earnings Presentation Q1 2021 April 23, 2021 Preface 2 Additional Information Corporate Headquarters 6565 Hillcrest Ave Dallas, TX 75205 Phone: 214-855-2177 www.hilltop-holdings.com Please Contact: Erik Yohe Phone: 214-525-4634 Email: [email protected] FORWARD-LOOKING STATEMENTS This presentation and statements made by representatives of Hilltop Holdings

February 17, 2021 EX-21.1

List of subsidiaries of the Registrant.

Exhibit 21.1 ? List of Subsidiaries of Hilltop Holdings Inc. As of February 16, 2021 ? ? ? ? Name State or Other Jurisdiction of Incorporation or Formation ARC Insurance Holdings, Inc. ? Delaware First Southwest Holdings LLC ? Delaware First Southwest Capital Investments, Inc. ? Delaware First Southwest Leasing Company ? Delaware FSC Asset Administrator, LLC ? Delaware Grand Home Loans, LLC ? Dela

February 17, 2021 10-K

Annual Report - 10-K

Table of Contents ? ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

February 17, 2021 EX-4.10

Description of the Registrant’s Securities (filed as Exhibit 4.10 to the Registrant’s Annual Report on Form 10-K for the year ended December 31, 2020 filed on February 17, 2021 (File No. 001-31987) and incorporated herein by reference).

Exhibit 4.10 ? DESCRIPTION OF THE REGISTRANT?S SECURITIES REGISTERED PURSUANT TO SECTION 12 OF THE SECURITIES EXCHANGE ACT OF 1934 ? Hilltop Holdings Inc. (?Hilltop,? ?we,? ?us,? or ?our?) has common stock registered under Section 12 of the Securities Exchange Act of 1934, as amended (the ?Exchange Act?). ? The following is a brief description of the terms of our capital stock. This summary does n

February 12, 2021 SC 13G/A

SCHEDULE 13G

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 4 )* Hilltop Holdings Inc (Name of Issuer) Common Stock (Title of Class of Securities) 432748101 (CUSIP Number) December 31, 2020 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which this S

February 10, 2021 SC 13G/A

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 (Amendment No.: 5)*

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 (Amendment No.: 5)* Name of issuer: Hilltop Holdings Inc. Title of Class of Securities: Common Stock CUSIP Number: 432748101 Date of Event Which Requires Filing of this Statement: December 31, 2020 Check the appropriate box to designate the rule pursuant to which this Schedule is filed:

January 28, 2021 EX-99.1

December 31,

Exhibit 99.1 Investor Relations Contact: Erik Yohe 214-525-4634 [email protected] Hilltop Holdings Inc. Announces Financial Results for Fourth Quarter and Full Year 2020 DALLAS — (BUSINESS WIRE) January 28, 2021 — Hilltop Holdings Inc. (NYSE: HTH) (“Hilltop”) today announced financial results for the fourth quarter and full year 2020. Hilltop produced income from continuing operations to

January 28, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 28, 2021 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission Fi

January 28, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 ? FORM 8-K ? CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 ? Date of Report (Date of earliest event reported): January 28, 2021 ? Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) ? ? ? ? ? ? Maryland ? 1-31987 ? 84-1477939 (State or other jurisdiction of incor

January 28, 2021 EX-99.1

Q4 2020 Hilltop Holdings Inc. Earnings Presentation January 2021 3 Investor Highlights – ROAA1 .86% EPS – Diluted1 ROAE1 5.76% Notes: (1) Results are presented on a consolidated basis. (2) Loans HFI reflect loans held for investment excluding margin

Exhibit 99.1 Q4 2020 Hilltop Holdings Inc. Earnings Presentation January 2021 Preface 2 Additional Information Corporate Headquarters 6565 Hillcrest Ave Dallas, TX 75205 Phone: 214-855-2177 www.hilltop-holdings.com Please Contact: Erik Yohe Phone: 214-525-4634 Email: [email protected] FORWARD-LOOKING STATEMENTS This presentation and statements made by representatives of Hilltop Holdings I

November 18, 2020 SC TO-I/A

- SC TO-I/A

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO (Amendment No. 4) Tender Offer Statement under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act of 1934 Hilltop Holdings Inc. (Name of Subject Company (Issuer)) Hilltop Holdings Inc. (Names of filing Persons (Offeror and Issuer)) Common Stock, Par Value $0.01 per share (Title of Class of Securities) 432748101 (CUSIP N

November 18, 2020 EX-99.(A)(5)(IV)

Press release announcing final results of the Tender Offer, dated November 18, 2020.

Exhibit (a)(5)(iv) Media Contact: Ben Brooks 214-252-4047 [email protected] Investor Relations Contact: Erik Yohe 214-525-4634 [email protected] Hilltop Holdings Inc. Announces Final Results of Tender Offer DALLAS (November 18, 2020) — Hilltop Holdings Inc. (NYSE: HTH) (“Hilltop” or the “Company”) announced today the final results of its modified “Dutch auction” tender offer

November 16, 2020 SC TO-I/A

- SCHEDULE TO-I/A

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO (Amendment No. 3) Tender Offer Statement under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act of 1934 Hilltop Holdings Inc. (Name of Subject Company (Issuer)) Hilltop Holdings Inc. (Names of filing Persons (Offeror and Issuer)) Common Stock, Par Value $0.01 per share (Title of Class of Securities) 432748101 (CUSIP N

November 16, 2020 EX-99.(A)(5)(III)

Press release announcing preliminary results of the Tender Offer, dated November 16, 2020.

Exhibit (a)(5)(iii) Media Contact: Ben Brooks 214-252-4047 [email protected] Investor Relations Contact: Erik Yohe 214-525-4634 [email protected] Hilltop Holdings Inc. Announces Preliminary Results of Tender Offer DALLAS (November 16, 2020) — Hilltop Holdings Inc. (NYSE: HTH) (“Hilltop” or the “Company”) announced today the preliminary results of its modified “Dutch auction”

November 2, 2020 EX-99.(A)(1)(VIII)

Amended Form of Letter of Transmittal.

Exhibit (a)(1)(viii) AMENDED LETTER OF TRANSMITTAL To Tender Shares of Common Stock Pursuant to the Offer to Purchase Dated September 23, 2020 As Amended and Supplemented by the Supplement to the Offer to Purchase, Dated November 2, 2020 by HILLTOP HOLDINGS INC.

November 2, 2020 EX-99.(A)(1)(XI)

Supplemental form of letter to clients for use by brokers, dealers, commercial banks, trust companies and other nominees.

Exhibit (a)(1)(xi) Offer by HILLTOP HOLDINGS INC. to Purchase for Cash Up to $350,000,000 of its Common Stock At a Purchase Price Not Less Than $21.00 Per Share and Not More Than $24.00 Per Share THE TENDER OFFER, THE PRORATION PERIOD AND WITHDRAWAL RIGHTS EXPIRE AT 12:00 MIDNIGHT, NEW YORK CITY TIME, AT THE END OF THE DAY ON NOVEMBER 13, 2020, UNLESS THE TENDER OFFER IS EXTENDED OR TERMINATED. No

November 2, 2020 EX-99.(A)(1)(VII)

Supplement to the Offer to Purchase, dated November 2, 2020.

Exhibit (a)(1)(vii) HILLTOP HOLDINGS INC. Supplement to the Offer to Purchase for Cash Up to $350,000,000 of Its Common Stock to Increase the Purchase Price to Not Less Than $21.00 Per Share and Not More Than $24.00 Per Share THE TENDER OFFER, THE PRORATION PERIOD AND WITHDRAWAL RIGHTS EXPIRE AT 12:00 MIDNIGHT, NEW YORK CITY TIME, AT THE END OF THE DAY ON NOVEMBER 13, 2020, UNLESS THE TENDER OFFER

November 2, 2020 SC TO-I/A

- SC TO-I/A

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO (Amendment No. 2) Tender Offer Statement under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act of 1934 Hilltop Holdings Inc. (Name of Subject Company (Issuer)) Hilltop Holdings Inc. (Names of filing Persons (Offeror and Issuer)) Common Stock, Par Value $0.01 per share (Title of Class of Securities) 432748101 (CUSIP N

November 2, 2020 EX-99.(A)(1)(X)

Supplemental form of letter to brokers, dealers, commercial banks, trust companies and other nominees.

Exhibit (a)(1)(x) Offer by HILLTOP HOLDINGS INC. to Purchase for Cash Up to $350,000,000 of its Common Stock At a Purchase Price Not Less Than $21.00 Per Share and Not More Than $24.00 Per Share THE TENDER OFFER, THE PRORATION PERIOD AND WITHDRAWAL RIGHTS EXPIRE AT 12:00 MIDNIGHT, NEW YORK CITY TIME, AT THE END OF THE DAY ON NOVEMBER 13, 2020, UNLESS THE TENDER OFFER IS EXTENDED OR TERMINATED. Nov

November 2, 2020 EX-99.(A)(5)(II)

Press release announcing the amendment and extension of the Tender Offer, dated October 30, 2020.

Exhibit (a)(5)(ii) Media Contact: Ben Brooks 214-252-4047 [email protected] Investor Relations Contact: Erik Yohe 214-525-4634 [email protected] Hilltop Holdings Inc. Announces Increase in Price Range and Extension of Expiration Date of Current Modified Dutch Auction Tender Offer DALLAS (October 30, 2020) — Hilltop Holdings Inc. (NYSE: HTH) (“Hilltop” or the “Company”) annou

November 2, 2020 EX-99.(A)(1)(IX)

Amended Notice of Guaranteed Delivery.

Exhibit (a)(1)(ix) AMENDED NOTICE OF GUARANTEED DELIVERY (Not to Be Used For Signature Guarantee) To Tender Shares of Common Stock Pursuant to the Offer to Purchase Dated September 23, 2020 As Amended and Supplemented by the Supplement to the Offer to Purchase, Dated November 2, 2020 by HILLTOP HOLDINGS INC.

October 23, 2020 10-Q

Quarterly Report - 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2020 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Commission File Number: 1-31987 Hilltop Holdings Inc.

October 22, 2020 EX-99.1

September 30,

Exhibit 99.1 Investor Relations Contact: Erik Yohe 214-525-4634 [email protected] Hilltop Holdings Inc. Announces Financial Results for Third Quarter 2020 DALLAS — (BUSINESS WIRE) October 22, 2020 — Hilltop Holdings Inc. (NYSE: HTH) (“Hilltop”) today announced financial results for the third quarter of 2020. Hilltop produced income from continuing operations to common stockholders of $152

October 22, 2020 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition, Other Events - 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): October 22, 2020 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission Fi

October 22, 2020 EX-99.1

Hilltop Holdings Inc. Earnings Presentation Q3 2020 October 2020 3 Notes: (1) HTH Consolidated defined as continuing and discontinued operations. (2) For a reconciliation of tangible book value per share to book value per share see management’s expla

Exhibit 99.1 Hilltop Holdings Inc. Earnings Presentation Q3 2020 October 2020 Preface 2 Additional Information Corporate Headquarters 6565 Hillcrest Ave Dallas, TX 75205 Phone: 214-855-2177 www.hilltop-holdings.com Please Contact: Erik Yohe Phone: 214-525-4634 Email: [email protected] FORWARD-LOOKING STATEMENTS This presentation and statements made by representatives of Hilltop Holdings I

October 22, 2020 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition - 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): October 22, 2020 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission Fi

September 29, 2020 CORRESP

-

[Letterhead of Wachtell, Lipton, Rosen & Katz] VIA EDGAR U.S. Securities and Exchange Commission Division of Corporation Finance 100 F. Street, N.E. Washington, D.C. 20549 Attention: Nicholas P. Panos Re: Hilltop Holdings Inc. Schedule TO-I Filed September 23, 2020 File No. 005-79781 Dear Mr. Panos: On behalf of our client, Hilltop Holdings Inc. (the “Company”), set forth below are responses to co

September 29, 2020 SC TO-I/A

- SC TO-I/A

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO (Amendment No. 1) Tender Offer Statement under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act of 1934 Hilltop Holdings Inc. (Name of Subject Company (Issuer)) Hilltop Holdings Inc. (Names of filing Persons (Offeror and Issuer)) Common Stock, Par Value $0.01 per share (Title of Class of Securities) 432748101 (CUSIP N

September 23, 2020 EX-99.(A)(1)(III)

Notice of Guaranteed Delivery.

Exhibit (a)(1)(iii) NOTICE OF GUARANTEED DELIVERY (Not to Be Used For Signature Guarantee) To Tender Shares of Common Stock Pursuant to the Offer to Purchase Dated September 23, 2020 by HILLTOP HOLDINGS INC.

September 23, 2020 EX-99.(A)(1)(IV)

Letter to brokers, dealers, commercial banks, trust companies and other nominees, dated September 23, 2020.

Exhibit (a)(1)(iv) Offer by HILLTOP HOLDINGS INC. to Purchase for Cash Up to $350,000,000 of its Common Stock At a Purchase Price Not Less Than $18.25 Per Share and Not More Than $21.00 Per Share THE TENDER OFFER, THE PRORATION PERIOD AND WITHDRAWAL RIGHTS EXPIRE AT 12:00 MIDNIGHT, NEW YORK CITY TIME, AT THE END OF THE DAY ON OCTOBER 30, 2020, UNLESS THE TENDER OFFER IS EXTENDED OR TERMINATED. Sep

September 23, 2020 EX-99.(A)(5)(I)

Press release announcing the Tender Offer, dated September 23, 2020.

Exhibit (a)(5)(i) Media Contact: Ben Brooks 214-252-4047 [email protected] Investor Relations Contact: Erik Yohe 214-525-4634 [email protected] Hilltop Holdings Inc. Commences a Modified Dutch Auction Tender Offer to Repurchase up to $350.0 Million of its Common Stock DALLAS (September 23, 2020) — Hilltop Holdings Inc. (NYSE: HTH) (“Hilltop” or the “Company”) announced today

September 23, 2020 SC TO-I

- SC TO-I

SC TO-I 1 tm2031463d1sctoi.htm SC TO-I As filed with the Securities and Exchange Commission on September 23, 2020 SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO Tender Offer Statement under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act of 1934 Hilltop Holdings Inc. (Name of Subject Company (Issuer)) Hilltop Holdings Inc. (Names of filing Persons (Offeror and Is

September 23, 2020 EX-99.(A)(1)(II)

Form of Letter of Transmittal.

Exhibit (a)(1)(ii) LETTER OF TRANSMITTAL To Tender Shares of Common Stock Pursuant to the Offer to Purchase Dated September 23, 2020 by HILLTOP HOLDINGS INC.

September 23, 2020 EX-99.(A)(1)(VI)

Summary Advertisement, dated September 23, 2020.

Exhibit (a)(1)(vi) This announcement is neither an offer to purchase nor a solicitation of an offer to sell shares of Hilltop Holdings Inc.

September 23, 2020 EX-99.(A)(1)(V)

Letter to clients for use by brokers, dealers, commercial banks, trust companies and other nominees, dated September 23, 2020.

Exhibit (a)(1)(v) Offer by HILLTOP HOLDINGS INC. to Purchase for Cash Up to $350,000,000 of its Common Stock At a Purchase Price Not Less Than $18.25 Per Share and Not More Than $21.00 Per Share THE TENDER OFFER, THE PRORATION PERIOD AND WITHDRAWAL RIGHTS EXPIRE AT 12:00 MIDNIGHT, NEW YORK CITY TIME, AT THE END OF THE DAY ON OCTOBER 30, 2020, UNLESS THE TENDER OFFER IS EXTENDED OR TERMINATED. Sept

September 23, 2020 EX-99.(A)(1)(I)

Offer to Purchase, dated September 23, 2020.

Exhibit (a)(1)(i) HILLTOP HOLDINGS INC. Offer to Purchase for Cash Up to $350,000,000 of its Common Stock At a Purchase Price Not Less Than $18.25 Per Share and Not More Than $21.00 Per Share CUSIP: 432748101 THE TENDER OFFER, THE PRORATION PERIOD AND WITHDRAWAL RIGHTS EXPIRE AT 12:00 MIDNIGHT, NEW YORK CITY TIME, AT THE END OF THE DAY ON OCTOBER 30, 2020, UNLESS THE TENDER OFFER IS EXTENDED OR TE

August 21, 2020 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 20, 2020 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission Fil

July 31, 2020 EX-99.1

June 30,

Exhibit 99.1 Investor Relations Contact: Erik Yohe 214-525-4634 [email protected] Hilltop Holdings Inc. Announces Financial Results for Second Quarter 2020 DALLAS — (BUSINESS WIRE) July 30, 2020 — Hilltop Holdings Inc. (NYSE: HTH) (“Hilltop”) today announced financial results for the second quarter of 2020. Hilltop produced income from continuing operations to common stockholders of $97.7

July 31, 2020 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 30, 2020 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission File

July 31, 2020 EX-99.1

Hilltop Holdings Inc. Earnings Presentation Q2 2020 July 2020 3 COVID-19 Response and Customer Support Update Customer Support Operations and Employee Health • Essential employees are working from corporate offices and bank branches; the majority of

Exhibit 99.1 Hilltop Holdings Inc. Earnings Presentation Q2 2020 July 2020 Preface 2 Additional Information Corporate Headquarters 6565 Hillcrest Ave Dallas, TX 75205 Phone: 214-855-2177 www.hilltop-holdings.com Please Contact: Erik Yohe Phone: 214-525-4634 Email: [email protected] FORWARD-LOOKING STATEMENTS This presentation and statements made by representatives of Hilltop Holdings Inc.

July 31, 2020 10-Q

Quarterly Report - 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2020 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Commission File Number: 1-31987 Hilltop Holdings Inc.

July 31, 2020 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition, Other Events - 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 30, 2020 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission File

July 29, 2020 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 23, 2020 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission File

July 27, 2020 8-K

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 23, 2020 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission File

July 24, 2020 EX-99.5

Form of Restricted Stock Unit Award Agreement (Time-Based Vesting for Non-Section 16 Officers) for awards beginning in 2020 (filed as Exhibit 99.5 to the Registrant’s Registration Statement on Form S-8 filed on July 24, 2020 (File No. 333-240090) and incorporated herein by reference).

Exhibit 99.5 RESTRICTED STOCK UNIT AWARD AGREEMENT THIS RESTRICTED STOCK UNIT AWARD AGREEMENT (this “Agreement”), dated as of , between Hilltop Holdings Inc., a Maryland corporation (the “Company”), and (the “Participant”). W I T N E S S E T H In consideration of the mutual promises and covenants made herein and the mutual benefits to be derived herefrom, the parties hereto agree as follows: 1. Gr

July 24, 2020 EX-99.1

Hilltop Holdings Inc. 2020 Equity Incentive Plan, effective April 30, 2020 (filed as Exhibit 99.1 to the Registrant’s Registration Statement on Form S-8 filed on July 24, 2020 (File No. 333-240090) and incorporated herein by reference).

Exhibit 99.1 HILLTOP HOLDINGS INC. 2020 EQUITY INCENTIVE PLAN The Hilltop Holdings Inc. 2020 Equity Incentive Plan (the “Plan”) was adopted by the Board of Directors of Hilltop Holdings Inc., a Maryland corporation (the “Company”), effective as of April 30, 2020 (the “Effective Date”), subject to approval by the Company’s stockholders. Article 1. PURPOSE The purpose of the Plan is to attract and r

July 24, 2020 EX-99.2

Hilltop Holdings Inc. Employee Stock Purchase Plan, effective April 30, 2020 (filed as Exhibit 99.2 to the Registrant’s Registration Statement on Form S-8 filed on July 24, 2020 (File No. 333-240090) and incorporated herein by reference).

Exhibit 99.2 HILLTOP HOLDINGS INC. EMPLOYEE STOCK PURCHASE PLAN The Hilltop Holdings Inc. Employee Stock Purchase Plan (the “Plan”) was adopted by the Board of Directors of Hilltop Holdings Inc., a Maryland corporation (the “Company”), effective as of April 30, 2020 (the “Effective Date”), subject to approval by the Company’s stockholders. 1. General. (a) The purpose of the Plan is to provide a me

July 24, 2020 S-8

Form S-8 (File No. 333-240090) filed with the Commission on July 24, 2020

As filed with the Securities and Exchange Commission on July 24, 2020 Registration No.

July 24, 2020 EX-99.3

Form of Restricted Stock Unit Award Agreement (Performance-Based) for awards beginning in 2020 (filed as Exhibit 99.3 to the Registrant’s Registration Statement on Form S-8 filed on July 24, 2020 (File No. 333-240090) and incorporated herein by reference).

Exhibit 99.3 RESTRICTED STOCK UNIT AWARD AGREEMENT THIS RESTRICTED STOCK UNIT AWARD AGREEMENT (this “Agreement”), dated as of , between Hilltop Holdings Inc., a Maryland corporation (the “Company”), and (the “Participant”). W I T N E S S E T H In consideration of the mutual promises and covenants made herein and the mutual benefits to be derived herefrom, the parties hereto agree as follows: 1. Gr

July 24, 2020 EX-99.4

Form of Restricted Stock Unit Award Agreement (Time-Based Vesting for Section 16 Officers) for awards beginning in 2020 (filed as Exhibit 99.4 to the Registrant’s Registration Statement on Form S-8 filed on July 24, 2020 (File No. 333-240090) and incorporated herein by reference).

Exhibit 99.4 RESTRICTED STOCK UNIT AWARD AGREEMENT THIS RESTRICTED STOCK UNIT AWARD AGREEMENT (this “Agreement”), dated as of , between Hilltop Holdings Inc., a Maryland corporation (the “Company”), and (the “Participant”). W I T N E S S E T H In consideration of the mutual promises and covenants made herein and the mutual benefits to be derived herefrom, the parties hereto agree as follows: 1. Gr

July 9, 2020 DEFA14A

- DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant x Filed by a Party other than the Registrant ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ¨ Defin

July 1, 2020 EX-99.1

Hilltop Holdings Inc. Completes Sale of National Lloyds Corporation to Align Financial Holdings, LLC

Exhibit 99.1 Hilltop Media Contact: Align Media Contact: Ben Brooks | 214.252.4047 Kieran Sweeney | 619.333.2501 [email protected] [email protected] Hilltop Investor Relations Contact: Erik Yohe | 214.525.4634 [email protected] Hilltop Holdings Inc. Completes Sale of National Lloyds Corporation to Align Financial Holdings, LLC DALLAS (July 1, 2020) – Hilltop Holdings

July 1, 2020 EX-2.2

First Amendment to Stock Purchase Agreement by and among Hilltop Holdings Inc., ARC Insurance Holdings, Inc., Align NL Holdings, LLC and, for limited purposes set forth therein, Align Financial Holdings, LLC and MGI Holdings, Inc., dated June 30, 2020 (filed as Exhibit 2.2 to the Registrant’s Current Report on Form 8-K filed July 1, 2020 (File No. 001-31987) and incorporated herein by reference).

Exhibit 2.2 EXECUTION VERSION FIRST AMENDMENT TO STOCK PURCHASE AGREEMENT This First Amendment to Stock Purchase Agreement (this “Amendment”) is entered into as of June 30, 2020, by and among Hilltop Holdings Inc., a Maryland corporation (“Hilltop”), ARC Insurance Holdings, Inc., a Delaware corporation and a direct wholly owned subsidiary of Hilltop (“ARC Insurance Holdings,” and collectively with

July 1, 2020 8-K

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Completion of Acquisition or Disposition of Assets, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): June 30, 2020 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission File

May 13, 2020 EX-4.2

First Supplemental Indenture, dated as of May 11, 2020, between Hilltop Holdings Inc., as Issuer, and U.S. Bank National Association, as Trustee (filed as Exhibit 4.2 to the Registrant’s Current Report on Form 8-K filed May 13, 2020 (File No. 001-31987) and incorporated herein by reference).

Exhibit 4.2 Execution Version HILLTOP HOLDINGS INC., as Issuer and U.S. BANK NATIONAL ASSOCIATION, as Trustee FIRST SUPPLEMENTAL INDENTURE Dated as of May 11, 2020 to Indenture dated as of May 11, 2020 5.75% Fixed-to-Floating Rate Subordinated Notes due 2030 TABLE OF CONTENTS Page No. ARTICLE I DEFINITIONS 1 Section 1.1 Definition of Terms 1 Section 1.2 Rules of Construction 11 ARTICLE II GENERAL

May 13, 2020 EX-1.1

Underwriting Agreement, dated as of May 7, 2020, by and among Hilltop Holdings Inc., Piper Sandler & Co. and U.S. Bancorp Investments, Inc.

Exhibit 1.1 $50,000,000 Aggregate Principal Amount of 5.75% Fixed-to-Floating Rate Subordinated Notes due 2030 $150,000,000 Aggregate Principal Amount of 6.125% Fixed-to-Floating Rate Subordinated Notes due 2035 Hilltop Holdings Inc. UNDERWRITING AGREEMENT May 7, 2020 PIPER SANDLER & CO. U.S. BANCORP INVESTMENTS, INC. As Representatives of the several Underwriters c/o PIPER SANDLER & CO. 1251 Aven

May 13, 2020 EX-4.3

Second Supplemental Indenture, dated as of May 11, 2020, between Hilltop Holdings Inc., as Issuer, and U.S. Bank National Association, as Trustee (filed as Exhibit 4.3 to the Registrant’s Current Report on Form 8-K filed May 13, 2020 (File No. 001-31987) and incorporated herein by reference).

Exhibit 4.3 Execution Version HILLTOP HOLDINGS INC., as Issuer and U.S. BANK NATIONAL ASSOCIATION, as Trustee SECOND SUPPLEMENTAL INDENTURE Dated as of May 11, 2020 to Indenture dated as of May 11, 2020 6.125% Fixed-to-Floating Rate Subordinated Notes due 2035 TABLE OF CONTENTS Page No. ARTICLE I DEFINITIONS 2 Section 1.1 Definition of Terms 2 Section 1.2 Rules of Construction 11 ARTICLE II GENERA

May 13, 2020 EX-4.1

Indenture, dated as of May 11, 2020, between Hilltop Holdings Inc., as Issuer, and U.S. Bank National Association, as Trustee (filed as Exhibit 4.1 to the Registrant’s Current Report on Form 8-K filed May 13, 2020 (File No. 001-31987) and incorporated herein by reference).

Exhibit 4.1 Execution Version HILLTOP HOLDINGS INC. as Issuer and U.S. Bank National Association as Trustee Indenture Dated as of May 11, 2020 Subordinated Debt Securities HILLTOP HOLDINGS INC. Reconciliation and tie between Trust Indenture Act of 1939 and Indenture, dated as of May 11, 2020 Section of Trust Indenture Act of 1939 Section(s) of Indenture § 310 (a)(1) 7.10 (a)(2) 7.10 (a)(3) Not App

May 13, 2020 8-K

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 7, 2020 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission File Nu

May 8, 2020 424B5

Title of Each Class of Securities to be Registered Proposed Maximum Aggregate Offering Price Registration Fee(1)(2)(3) 5.75% Fixed-to-Floating Rate Subordinated Notes due 2030 $50,000,000 $6,490 6.125% Fixed-to-Floating Rate Subordinated Notes due 20

424B5 1 a2241589z424b5.htm 424B5 Use these links to rapidly review the document TABLE OF CONTENTS TABLE OF CONTENTS Filed Pursuant to Rule 424(b)(5) File No. 333-237447 Title of Each Class of Securities to be Registered Proposed Maximum Aggregate Offering Price Registration Fee(1)(2)(3) 5.75% Fixed-to-Floating Rate Subordinated Notes due 2030 $50,000,000 $6,490 6.125% Fixed-to-Floating Rate Subord

May 8, 2020 FWP

Hilltop Holdings Inc. $50,000,000 5.75% Fixed-to-Floating Rate Subordinated Notes due 2030 $150,000,000 6.125 % Fixed-to-Floating Rate Subordinated Notes due 2035 Pricing Term Sheet

Filed Pursuant to Rule 433 Supplementing the Preliminary Prospectus Supplement, dated May 7, 2020 Issuer Free Writing Prospectus dated May 7, 2020 Registration No.

May 7, 2020 424B5

SUBJECT TO COMPLETION PRELIMINARY PROSPECTUS SUPPLEMENT DATED MAY 7, 2020

Use these links to rapidly review the document TABLE OF CONTENTS TABLE OF CONTENTS Table of Contents Filed Pursuant to Rule 424(b)(5) File No.

May 7, 2020 EX-99.1

Corporate Headquarters Additional Information Dallas, TX 75205 Erik Yohe Phone: 214-855-2177 Phone: 214-525-4634 www.hilltop-holdings.com Email: [email protected]

Exhibit 99.1 Hilltop Holdings Inc. Investor Presentation May 7, 2020 Preface Corporate Headquarters Additional Information 6565 Hillcrest Ave Please Contact: Dallas, TX 75205 Erik Yohe Phone: 214-855-2177 Phone: 214-525-4634 www.hilltop-holdings.com Email: [email protected] FORWARD-LOOKING STATEMENTS This presentation and statements made by representatives of Hilltop Holdings Inc. (“Hillt

May 7, 2020 8-K

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 7, 2020 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission File Nu

May 5, 2020 EX-10.1

Form of Restricted Stock Unit Award Agreement (Performance-Based Vesting) for awards beginning in 2020 (filed as Exhibit 10.1 to the Registrant’s Quarterly Report on Form 10-Q filed on May 5, 2020 (File No. 001-31987) and incorporated herein by reference).

Exhibit 10.1 Form of RESTRICTED STOCK UNIT AWARD AGREEMENT THIS RESTRICTED STOCK UNIT AWARD AGREEMENT (this “Agreement”), dated as of the day of , between Hilltop Holdings Inc., a Maryland corporation (the “Company”), and (the “Participant”). W I T N E S S E T H In consideration of the mutual promises and covenants made herein and the mutual benefits to be derived herefrom, the parties hereto agre

May 5, 2020 EX-10.3

Form of Restricted Stock Unit Award Agreement (Time-Based Vesting for Non-Section 16 Officers) for awards beginning in 2020 (filed as Exhibit 10.3 to the Registrant’s Quarterly Report on Form 10-Q filed on May 5, 2020 (File No. 001-31987) and incorporated herein by reference).

Exhibit 10.3 FORM OF RESTRICTED STOCK UNIT AWARD AGREEMENT THIS RESTRICTED STOCK UNIT AWARD AGREEMENT (this “Agreement”), dated as of the day of 20, between Hilltop Holdings Inc., a Maryland corporation (the “Company”), and (the “Participant”). W I T N E S S E T H In consideration of the mutual promises and covenants made herein and the mutual benefits to be derived herefrom, the parties hereto ag

May 5, 2020 EX-10.2

Form of Restricted Stock Unit Award Agreement (Time-Based Vesting for Section 16 Officers) for awards beginning in 2020 (filed as Exhibit 10.2 to the Registrant’s Quarterly Report on Form 10-Q filed on May 5, 2020 (File No. 001-31987) and incorporated herein by reference).

Exhibit 10.2 FORM OF RESTRICTED STOCK UNIT AWARD AGREEMENT THIS RESTRICTED STOCK UNIT AWARD AGREEMENT (this “Agreement”), dated as of the day of 20, between Hilltop Holdings Inc., a Maryland corporation (the “Company”), and (the “Participant”). W I T N E S S E T H In consideration of the mutual promises and covenants made herein and the mutual benefits to be derived herefrom, the parties hereto ag

May 5, 2020 10-Q

Quarterly Report - 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2020 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Commission File Number: 1-31987 Hilltop Holdings Inc.

May 4, 2020 EX-99.1

Hilltop Holdings Inc. Investor Presentation May 2020

Exhibit 99.1 Hilltop Holdings Inc. Investor Presentation May 2020 Preface Corporate Headquarters 6565 Hillcrest Ave Dallas, TX 75205 Phone: 214-855-2177 www.hilltop-holdings.com Additional Information Please Contact: Erik Yohe Phone: 214-525-4634 Email: [email protected] FORWARD-LOOKING STATEMENTS This presentation and statements made by representatives of Hilltop Holdings Inc. (“Hilltop”

May 4, 2020 8-K

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 4, 2020 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission File Nu

April 30, 2020 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 30, 2020 Hilltop Holdings Inc. (Exact name of registrant as specified in its charter) Maryland 1-31987 84-1477939 (State or other jurisdiction of incorporation) (Commission File

April 30, 2020 EX-99.1

March 31,

Exhibit 99.1 Investor Relations Contact: Erik Yohe 214-525-4634 [email protected] Hilltop Holdings Inc. Announces Financial Results for First Quarter 2020 DALLAS — (BUSINESS WIRE) April 30, 2020 — Hilltop Holdings Inc. (NYSE: HTH) (“Hilltop”) today announced financial results for the first quarter of 2020. Hilltop produced income from continuing operations to common stockholders of $46.5

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