WTFCP / Wintrust Financial Corporation - Preferred Stock - Pemfailan SEC, Laporan Tahunan, Penyata Proksi

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

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 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 OR ☐ 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 001-35077 WINT

Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018

Exhibit 99.1 Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018 News Release FOR IMMEDIATE RELEASE July 21, 2025 FOR MORE INFORMATION CONTACT: David A. Dykstra, Vice Chairman & Chief Operating Officer (847) 939-9000 Amy Yuhn, Executive Vice President, Communications (847) 939-9591 Web site address: www.wintrust.com Wintrust Financial Corporation Reports Record

Earnings Release Presentation Q2 2025 Wintrust Financial Corporation 22 This document contains forward-looking statements within the meaning of federal securities laws. Forward-looking information can be identified through the use of words such as “i

q22025earningsrelease Earnings Release Presentation Q2 2025 Wintrust Financial Corporation 22 This document contains forward-looking statements within the meaning of federal securities laws.

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, 2025 WINTRUST FINANCIAL

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, 2025 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Commi

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 15, 2025 WINTRUST FINANCIAL

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 15, 2025 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Commi

Statement of Resolution of the Board of Directors of Wintrust Financial Corporation Regarding the Series E Preferred Stock.

Exhibit 3.2 FORM BCA 6.10 (rev. Dec. 2003) STATEMENT OF RESOLUTION ESTABLISHING SERIES Business Corporation Act Secretary of State Department of Business Services 501 S. Second St., Rm. 350 Springfield, IL 62756 217-782-6961 www.ilsos.gov Remit payment in the form of a check or money order payable to Secretary of State. File # Filing Fee: $25          Approved: – – – – Submit in duplicate – – – –

Statement of Resolution of the Board of Directors of Wintrust Financial Corporation Regarding the Series D Preferred Stock.

Exhibit 3.1 FORM BCA 6.10 (rev. Dec. 2003) STATEMENT OF RESOLUTION ESTABLISHING SERIES Business Corporation Act Secretary of State Department of Business Services 501 S. Second St., Rm. 350 Springfield, IL 62756 217-782-6961 www.ilsos.gov Remit payment in the form of a check or money order payable to Secretary of State. File # Filing Fee: $25          Approved: – – – – Submit in duplicate – – – –

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 11, 2025 WINTRUST FINANCIAL

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 11, 2025 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Commi

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 13, 2025 WINTRUST FINANCIAL

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 13, 2025 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Commi

June 13, 2025

Exhibit 99.1 FOR IMMEDIATE RELEASE June 13, 2025 FOR MORE INFORMATION CONTACT: Timothy S. Crane, President & Chief Executive Officer David A. Dykstra, Vice Chairman & Chief Operating Officer (847) 939-9000 Wintrust Financial Corporation Announces Redemption of All Outstanding Series D and Series E Preferred Stock and Related Depositary Shares ROSEMONT, IL ⸺ Wintrust Financial Corporation (“Wintrus

Wintrust Financial Corporation 2025 Stock Incentive Plan

EXHIBIT 10.1 WINTRUST FINANCIAL CORPORATION 2025 STOCK INCENTIVE PLAN 1.Purpose; Effect on Predecessor Plan. The purpose of the Wintrust Financial Corporation 2025 Stock Incentive Plan is to benefit the Corporation and its Subsidiaries by enabling the Corporation to offer certain present and future officers, employees, directors and consultants stock-based incentives and other equity interests in

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits, 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): May 22, 2025 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Commis

Deposit Agreement, dated as of May 22, 2025, among Wintrust Financial Corporation, U.S. Bank Trust Company, National Association, as Depositary, and the holders from time to time of the Depositary Receipts issued thereunder.

Exhibit 4.2 DEPOSIT AGREEMENT among Wintrust Financial Corporation, as Issuer U.S. Bank Trust Company, National Association, as Depositary, and THE HOLDERS FROM TIME TO TIME OF THE DEPOSITARY RECEIPTS DESCRIBED HEREIN Dated as of May 22, 2025 TABLE OF CONTENTS Page ARTICLE I DEFINED TERMS 1 Section 1.1. Definitions 1 ARTICLE II FORM OF RECEIPTS, DEPOSIT OF STOCK, EXECUTION AND DELIVERY, TRANSFER,

As filed with the Securities and Exchange Commission on May 22, 2025

As filed with the Securities and Exchange Commission on May 22, 2025 Registration No.

Filing Fee Table.

Calculation of Filing Fee Tables S-8 WINTRUST FINANCIAL CORP Table 1: Newly Registered Securities Security Type Security Class Title Fee Calculation Rule Amount Registered Proposed Maximum Offering Price Per Unit Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee 1 Equity Common Stock, no par value per share 457(a) 2,181,300 $ 121.

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 22, 2025 WINTRUST FINANCIAL C

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 22, 2025 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Commis

Form of Deposit Agreement, by and among the Company, U.S. Bank Trust Company, National Association, as registrar and as depositary, and the holders from time to time of the depositary receipts described therein.

Exhibit 4.1 DEPOSIT AGREEMENT among Wintrust Financial Corporation, as Issuer U.S. Bank Trust Company, National Association, as Depositary, and THE HOLDERS FROM TIME TO TIME OF THE DEPOSITARY RECEIPTS DESCRIBED HEREIN Dated as of May 22, 2025 TABLE OF CONTENTS Page ARTICLE I DEFINED TERMS 1 Section 1.1. Definitions 1 ARTICLE II FORM OF RECEIPTS, DEPOSIT OF STOCK, EXECUTION AND DELIVERY, TRANSFER,

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 12(g) OF THE SECURITIES EXCHANGE ACT OF 1934 WINTRUST FINANCIAL CORPORATION (Exact name of

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 12(g) OF THE SECURITIES EXCHANGE ACT OF 1934 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 36-3873352 (State or other jurisdiction of incorporation or organization) (I.R.S. Employer Identific

Certificate of Designation of Wintrust Financial Corporation filed on May 9, 2025 with the Secretary of the State of Illinois designating the preferences, limitation, voting powers and relative rights of the Series F Preferred Stock (incorporated by reference to Exhibit 3.1 to the Company’s Current Report on Form 8-K, filed with the Securities and Exchange Commission on May 14, 2025).

Exhibit 3.1 WINTRUST FINANCIAL CORPORATION CERTIFICATE OF DESIGNATIONS Pursuant to Section 6.10 of the Illinois Business Corporation Act 7.875% FIXED-RATE RESET NON-CUMULATIVE PERPETUAL PREFERRED STOCK, SERIES F (no par value per share) The undersigned, David A. Dykstra, Vice Chairman and Chief Operating Officer of Wintrust Financial Corporation, an Illinois corporation (the “Corporation”), hereby

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 9, 2025 WINTRUST FINANCIAL CO

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 9, 2025 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Commiss

Wintrust Financial Corporation 17,000,000 Depositary Shares, Each Representing a 1/1,000th Interest in a Share of 7.875% Fixed-Rate Reset Non-Cumulative Perpetual Preferred Stock, Series F

TABLE OF CONTENTS  Filed Pursuant to Rule 424(b)(5)  File No. 333-271788 PROSPECTUS SUPPLEMENT (To prospectus dated May 9, 2023) Wintrust Financial Corporation 17,000,000 Depositary Shares, Each Representing a 1/1,000th Interest in a Share of 7.875% Fixed-Rate Reset Non-Cumulative Perpetual Preferred Stock, Series F We are offering to sell 17,000,000 depositary shares, each representing a 1/1,000t

Table 1: Newly Registered and Carry Forward Securities

Calculation of Filing Fee Tables S-3 WINTRUST FINANCIAL CORP Table 1: Newly Registered and Carry Forward Securities Security Type Security Class Title Fee Calculation or Carry Forward Rule Amount Registered Proposed Maximum Offering Price Per Unit Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee Carry Forward Form Type Carry Forward File Number Carry Forward Initial Effective Date Filing Fee Previously Paid in Connection with Unsold Securities to be Carried Forward Newly Registered Securities Fees to be Paid 1 Equity Depositary Shares, Each Representing a 1/1,000th Interest in a Share of 7.

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 8, 2025 WINTRUST FINANCIAL CO

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 8, 2025 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Commiss

Underwriting Agreement, dated as of May 8, 2025, between Wintrust Financial Corporation and RBC Capital Markets, LLC, as representative of the several underwriters named in Schedule A thereto.

Exhibit 1.1 EXECUTION COPY WINTRUST FINANCIAL CORPORATION (an Illinois corporation) 17,000,000 Depositary Shares, Each Representing a 1/1000th Interest in a Share of 7.875% Fixed-Rate Reset Non-Cumulative Perpetual Preferred Stock, Series F UNDERWRITING AGREEMENT May 8, 2025 RBC Capital Markets, LLC as Representative of the several Underwriters c/o RBC Capital Markets, LLC Brookfield Place 200 Ves

Wintrust Financial Corporation 17,000,000 DEPOSITARY SHARES, EACH REPRESENTING A 1/1,000th INTEREST IN A SHARE OF 7.875% FIXED-RATE RESET NON-CUMULATIVE PERPETUAL PREFERRED STOCK, SERIES F (liquidation preference $25,000 per share (equivalent to $25.

Filed pursuant to Rule 433 Issuer Free Writing Prospectus, dated May 8, 2025 Supplementing the Preliminary Prospectus Supplement, dated May 8, 2025 Registration No.

Subject to Completion Preliminary Prospectus Supplement dated May 8, 2025

TABLE OF CONTENTS The information in this preliminary prospectus supplement is not complete and may be changed.

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

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 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 OR ☐ 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 001-35077 WIN

Earnings Release Presentation Q1 2025 Wintrust Financial Corporation 22 This document contains forward-looking statements within the meaning of federal securities laws. Forward-looking information can be identified through the use of words such as “i

Earnings Release Presentation Q1 2025 Wintrust Financial Corporation 22 This document contains forward-looking statements within the meaning of federal securities laws.

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, 2025 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Comm

Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018

Exhibit 99.1 Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018 News Release FOR IMMEDIATE RELEASE April 21, 2025 FOR MORE INFORMATION CONTACT: Timothy S. Crane, President & Chief Executive Officer David A. Dykstra, Vice Chairman & Chief Operating Officer (847) 939-9000 Web site address: www.wintrust.com Wintrust Financial Corporation Reports Record First Quar

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 934 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)) ¨ Definitive Proxy Statement x Definitive Additional Materials ¨ Soliciting Material under § 240.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 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)) ☒ Definitive Proxy Statement ☐ Definitive Additional Materials ☐ Soliciting Material under § 240.

Subsidiaries of the Registrant December 31, 2024 Subsidiary Jurisdiction Barrington Bank & Trust Company, N.A. United States Beverly Bank & Trust Company, N.A. United States Crystal Lake Bank & Trust Company, N.A. United States Chicago Deferred Excha

Exhibit 21.1 Subsidiaries of the Registrant December 31, 2024 Subsidiary Jurisdiction Barrington Bank & Trust Company, N.A. United States Beverly Bank & Trust Company, N.A. United States Crystal Lake Bank & Trust Company, N.A. United States Chicago Deferred Exchange Company, LLC Delaware Elektra Holding Company, LLC Delaware First Insurance Funding of Canada, Inc. Canada FIFC Edge International Co

WINTRUST FINANCIAL CORPORATION INSIDER TRADING AND CONFIDENTIALITY POLICY

Adopted Effective as of April 27, 2023 WINTRUST FINANCIAL CORPORATION INSIDER TRADING AND CONFIDENTIALITY POLICY This Policy confirms procedures which employees and directors of Wintrust Financial Corporation (“WTFC”) and any of its subsidiaries (collectively, “Wintrust” or the “Company”) must follow, as well as additional procedures that are applicable to Insiders (as defined below).

WINTRUST FINANCIAL CORPORATION POLICY ON RECOUPMENT OF INCENTIVE COMPENSATION

Exhibit 97.1 Adopted Effective October 26, 2023 WINTRUST FINANCIAL CORPORATION POLICY ON RECOUPMENT OF INCENTIVE COMPENSATION Introduction The Board of Directors (the “Board”) of Wintrust Financial Corporation (the “Company”) has adopted this Policy on Recoupment of Incentive Compensation (this “Policy”), which provides for the recoupment of compensation in certain circumstances in the event of a

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

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 001-35077 Wintrust Financial Corporatio

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 21, 2025 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Co

Earnings Release Presentation Q4 2024 Wintrust Financial Corporation 22 This document contains forward-looking statements within the meaning of federal securities laws. Forward-looking information can be identified through the use of words such as “i

Earnings Release Presentation Q4 2024 Wintrust Financial Corporation 22 This document contains forward-looking statements within the meaning of federal securities laws.

Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018

Exhibit 99.1 Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018 News Release FOR IMMEDIATE RELEASE January 21, 2025 FOR MORE INFORMATION CONTACT: Timothy S. Crane, President & Chief Executive Officer David A. Dykstra, Vice Chairman & Chief Operating Officer (847) 939-9000 Web site address: www.wintrust.com Wintrust Financial Corporation Reports Record Full Yea

Third Amendment to Amended and Restated Credit Agreement

EXHIBIT 10.1 EXECUTION VERSION Third Amendment to Amended and Restated Credit Agreement and First Amendment to Amended and Restated Pledge and Security Agreement RECITALS: Borrower, Lenders and Wells Fargo Bank, National Association, as the resigning administrative agent ("Wells Fargo" or the "Resigning Administrative Agent") have previously entered into that certain Amended and Restated Credit Ag

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

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 6, 2024 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Co

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

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 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 OR ☐ 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 001-35077

Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018

Exhibit 99.1 Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018 News Release FOR IMMEDIATE RELEASE October 21, 2024 FOR MORE INFORMATION CONTACT: Timothy S. Crane, President & Chief Executive Officer David A. Dykstra, Vice Chairman & Chief Operating Officer (847) 939-9000 Web site address: www.wintrust.com Wintrust Financial Corporation Reports Third Quarter a

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 21, 2024 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Co

Earnings Release Presentation Q3 2024 Wintrust Financial Corporation 22 This document contains forward-looking statements within the meaning of federal securities laws. Forward-looking information can be identified through the use of words such as “i

Earnings Release Presentation Q3 2024 Wintrust Financial Corporation 22 This document contains forward-looking statements within the meaning of federal securities laws.

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 29, 2024 WINTRUST FINANCIA

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 29, 2024 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Com

by Wintrust Financial Corporation in favor of CIBC Mellon Trust Company, Plaza Trust.

EXHIBIT 10.2 Performance Guarantee Confirmation Reference is made to a Performance Guarantee dated as of December 16, 2014 made by the undersigned in favour of the Purchaser (the “Performance Guarantee”). The undersigned acknowledges and confirms that the performance guarantee remains in full force and effect notwithstanding the entering into of this Twelfth Amending Agreement Dated as of the 29th

by CIBC Mellon Trust Company, in its capacity as trustee of Plaza Trust, by its Financial Service Agent, Royal Bank of Canada and acknowledged by First Insurance Funding of Canada Inc.

EXHIBIT 10.3 PLAZA TRUST c/o Royal Bank of Canada 200 Bay Street, Royal Bank Plaza 2nd Floor, North Tower Toronto, ON, M5J 2W7 August 29, 2024 First Insurance Funding of Canada Inc. c/o Wintrust Financial Corporation 9700 West Higgins Road, Suite 800 Rosemont, IL 60018 Attention: Mr. David Dykstra, Vice Chairman and Chief Operating Officer Dear Sirs: Receivables Purchase Agreement dated as of Dece

a Inc. and CIBC Mellon Trust Company, in its capacity as trustee of Pla

EXHIBIT 10.1 TWELFTH AMENDING AGREEMENT (First Insurance Funding of Canada Inc.) This Twelfth Amending Agreement made as of August 29, 2024. B E T W E E N: FIRST INSURANCE FUNDING OF CANADA INC. (hereinafter referred to as the “Seller” or the “Servicer”) - and - CIBC MELLON TRUST COMPANY, in its capacity as trustee of PLAZA TRUST, (hereinafter referred to as the “Purchaser”) RECITALS: WHEREAS the

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

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 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 OR ☐ 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 001-35077 WINT

Amended and Restated By-laws of the Company, as amended (incorporated by reference to Exhibit 3.1 of the Company’s Current Report on Form 8-K, filed with the Securities and Exchange Commission on August 1, 2024)

EXHIBIT 3.1 Adopted Effective August 1, 2024 AMENDED AND RESTATED BY-LAWS OF WINTRUST FINANCIAL CORPORATION (AN ILLINOIS CORPORATION) AS AMENDED ARTICLE I OFFICES Wintrust Financial Corporation (the “corporation”) shall continuously maintain in the State of Illinois a registered office and a registered agent whose office is identical with such registered office, and may have other offices within o

WINTRUST FINANCIAL CORPORATION COMPLETES ITS MERGER WITH MACATAWA BANK CORPORATION

Exhibit 99.1 FOR IMMEDIATE RELEASE August 1, 2024 FOR MORE INFORMATION CONTACT: Timothy S. Crane, President and CEO – Wintrust Financial Corporation, (847) 939-9000 David A. Dykstra, Vice Chair and COO – Wintrust Financial Corporation, (847) 939-9000 Richard L. Postma, Chairman – Macatawa Bank Corporation, (616) 392-1517 Wintrust Website address: www.wintrust.com Macatawa Website address: www.maca

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, 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): August 1, 2024 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Comm

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 17, 2024 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Commi

Earnings Release Presentation Q2 2024 Wintrust Financial Corporation 22 This document contains forward-looking statements within the meaning of federal securities laws. Forward-looking information can be identified through the use of words such as “i

Earnings Release Presentation Q2 2024 Wintrust Financial Corporation 22 This document contains forward-looking statements within the meaning of federal securities laws.

Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018

Exhibit 99.1 Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018 News Release FOR IMMEDIATE RELEASE July 17, 2024 FOR MORE INFORMATION CONTACT: Timothy S. Crane, President & Chief Executive Officer David A. Dykstra, Vice Chairman & Chief Operating Officer (847) 939-9000 Web site address: www.wintrust.com Wintrust Financial Corporation Reports Record Year-to-Dat

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 17, 2024 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Commi

Macatawa Bank Corporation

TABLE OF CONTENTS  Filed Pursuant to Rule 424(b)(3)  File No.333-279835 Macatawa Bank Corporation Wintrust Financial Corporation PROXY STATEMENT OF MACATAWA BANK CORPORATION PROSPECTUS OF WINTRUST FINANCIAL CORPORATION Merger Proposed — Your Vote Is Important DEAR MACATAWA SHAREHOLDERS: You are cordially invited to attend a special meeting of shareholders of Macatawa Bank Corporation (“Macatawa”),

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 17, 2024 WINTRUST FINANCIAL

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 17, 2024 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Commi

As filed with the Securities and Exchange Commission on June 13, 2024.

TABLE OF CONTENTS As filed with the Securities and Exchange Commission on June 13, 2024.

Form of proxy card.

Exhibit 99.1 THIS PROXY CARD IS VALID ONLY WHEN SIGNED AND DATED. KEEP THIS PORTION FOR YOUR RECORDS DETACH AND RETURN THIS PORTION ONLY TO VOTE, MARK BLOCKS BELOW IN BLUE OR BLACK INK AS FOLLOWS: Signature [PLEASE SIGN WITHIN BOX] Date Signature (Joint Owners) Date SCAN TO VIEW MATERIALS & VOTE 0 0 0 0 0 0 0 0 0 00006486601 R1.0.0.6 MACATAWA BANK CORPORATION 10753 MACATAWA DRIVE HOLLAND, MI 49424

WINTRUST FINANCIAL CORPORATION 9700 W. Higgins Road, Suite 800 Rosemont, Illinois 60018 June 13, 2024

WINTRUST FINANCIAL CORPORATION 9700 W. Higgins Road, Suite 800 Rosemont, Illinois 60018 June 13, 2024 VIA EDGAR Securities and Exchange Commission Division of Corporation Finance 100 F. Street, N.E. Washington, D.C. 20549 Attn: John Stickel Re: Wintrust Financial Corporation Registration Statement on Form S-4 File No. 333-279835 Request for Acceleration of Effective Date Dear Mr. Stickel: Pursuant

Filing Fee Table.

Exhibit 107 Calculation of Filing Fee Table Form S-4 (Form Type) Wintrust Financial Corporation (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered Securities Security Type Security Class Title Fee Calculation Rule Amount Registered Proposed Maximum Offering Price Per Unit Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee Carry Forward Form Type Carry Forward File Number Filing Fee Previously Paid in Connection with Unsold Securities to be Carried Forward Newly Registered Securities Fees to Be Paid Equity Common Stock, no par value Other 5,731,509 (1) $ 479,515,597.

As filed with the Securities and Exchange Commission on May 30, 2024.

TABLE OF CONTENTS As filed with the Securities and Exchange Commission on May 30, 2024.

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): May 23, 2024 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Commis

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

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 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 OR ☐ 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 001-35077 WIN

Employment Agreement dated as of September 8, 2015 between Wintrust Financial Corporation and Kathleen M. Boege. *

EMPLOYMENT AGREEMENT This Employment Agreement (the "Agreement") is made by and between Wintrust Financial Corporation ("Employer" or "Wintrust"), an Illinois bank holding company, and Kathleen M.

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 17, 2024 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Comm

Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018

Exhibit 99.1 Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018 News Release FOR IMMEDIATE RELEASE April 17, 2024 FOR MORE INFORMATION CONTACT: Timothy S. Crane, President & Chief Executive Officer David A. Dykstra, Vice Chairman & Chief Operating Officer (847) 939-9000 Web site address: www.wintrust.com Wintrust Financial Corporation Reports Record First Quar

Earnings Release Presentation Q1 2024 Wintrust Financial Corporation 22 This document contains forward-looking statements within the meaning of federal securities laws. Forward-looking information can be identified through the use of words such as “i

Earnings Release Presentation Q1 2024 Wintrust Financial Corporation 22 This document contains forward-looking statements within the meaning of federal securities laws.

  Voting and Support Agreement

  Exhibit 99.1   Voting and Support Agreement   This Voting and Support Agreement (this “Agreement”) is entered into as of April 15, 2024, by and among Wintrust Financial Corporation, an Illinois corporation (“Purchaser”), Macatawa Bank Corporation, a Michigan corporation (“Company”), and those Persons whose names appear on the signature page of this Agreement and who own or solely control the vot

Wintrust Financial Corporation Acquisition of Macatawa Bank Corporation: Strategic Expansion Into West Michigan With a High - Performing Banking Platform April 15, 2024

Exhibit 99.3 Wintrust Financial Corporation Acquisition of Macatawa Bank Corporation: Strategic Expansion Into West Michigan With a High - Performing Banking Platform April 15, 2024 2 Forward Looking Statements This communication contains forward - looking statements within the meaning of the federal securities laws relating to the propose d acquisition of Macatawa Bank Corporation (“Macatawa”) by

Entry into a Material Definitive Agreement, 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): April 15, 2024 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Comm

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 15, 2024 WINTRUST FINANCIAL

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 15, 2024 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Comm

WINTRUST FINANCIAL CORPORATION AND MACATAWA BANK CORPORATION ANNOUNCE PLANS TO MERGE

Exhibit 99.2 FOR IMMEDIATE RELEASE April 15, 2024 FOR MORE INFORMATION CONTACT: Timothy S. Crane, President and CEO – Wintrust Financial Corporation, (847) 939-9000 David A. Dykstra, Vice Chair and COO – Wintrust Financial Corporation, (847) 939-9000 Richard L. Postma, Chairman – Macatawa Bank Corporation, (616) 392-1517 Wintrust Website address: www.wintrust.com Macatawa Website address: www.maca

WINTRUST FINANCIAL CORPORATION AND MACATAWA BANK CORPORATION ANNOUNCE PLANS TO MERGE

Exhibit 99.2 FOR IMMEDIATE RELEASE April 15, 2024 FOR MORE INFORMATION CONTACT: Timothy S. Crane, President and CEO – Wintrust Financial Corporation, (847) 939-9000 David A. Dykstra, Vice Chair and COO – Wintrust Financial Corporation, (847) 939-9000 Richard L. Postma, Chairman – Macatawa Bank Corporation, (616) 392-1517 Wintrust Website address: www.wintrust.com Macatawa Website address: www.maca

Agreement and Plan of Merger, by and among Wintrust Financial Corporation, Leo Subsidiary LLC and Macatawa Bank Corporation, dated April 15, 2024. (The schedules to the Agreement and Plan of Merger have been omitted. The registrant hereby agrees to furnish supplementally a copy of any omitted schedules to the SEC upon request.)

  Exhibit 2.1   AGREEMENT AND PLAN OF MERGER   BY AND AMONG   WINTRUST FINANCIAL CORPORATION,   LEO SUBSIDIARY LLC   AND   MACATAWA BANK CORPORATION   Dated as of April 15, 2024         Table of Contents   ARTICLE I THE MERGER 1       1.1 Merger 1 1.2 The Closing 2 1.3 Effective Time of Merger 2 1.4 Additional Actions 2 1.5 Surviving Company 2 1.6 Reservation of Right to Revise Structure 3       A

Wintrust Financial Corporation Acquisition of Macatawa Bank Corporation: Strategic Expansion Into West Michigan With a High - Performing Banking Platform April 15, 2024

Exhibit 99.3 Wintrust Financial Corporation Acquisition of Macatawa Bank Corporation: Strategic Expansion Into West Michigan With a High - Performing Banking Platform April 15, 2024 2 Forward Looking Statements This communication contains forward - looking statements within the meaning of the federal securities laws relating to the propose d acquisition of Macatawa Bank Corporation (“Macatawa”) by

  Voting and Support Agreement

  Exhibit 99.1   Voting and Support Agreement   This Voting and Support Agreement (this “Agreement”) is entered into as of April 15, 2024, by and among Wintrust Financial Corporation, an Illinois corporation (“Purchaser”), Macatawa Bank Corporation, a Michigan corporation (“Company”), and those Persons whose names appear on the signature page of this Agreement and who own or solely control the vot

Agreement and Plan of Merger by and among Wintrust Financial Corporation, Leo Subsidiary LLC and Macatawa Bank Corporation dated April 15, 2024. Previously filed with the Commission on April 15, 2024 in Macatawa Bank Corporation's Current Report on Form 8-K, Exhibit 2.1. Here incorporated by reference.

  Exhibit 2.1   AGREEMENT AND PLAN OF MERGER   BY AND AMONG   WINTRUST FINANCIAL CORPORATION,   LEO SUBSIDIARY LLC   AND   MACATAWA BANK CORPORATION   Dated as of April 15, 2024         Table of Contents   ARTICLE I THE MERGER 1       1.1 Merger 1 1.2 The Closing 2 1.3 Effective Time of Merger 2 1.4 Additional Actions 2 1.5 Surviving Company 2 1.6 Reservation of Right to Revise Structure 3       A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 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)) ¨ Definitive Proxy Statement x Definitive Additional Materials ¨ Soliciting Material under § 240.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 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)) ☒ Definitive Proxy Statement ☐ Definitive Additional Materials ☐ Soliciting Material under § 240.

WINTRUST FINANCIAL CORPORATION POLICY ON RECOUPMENT OF INCENTIVE COMPENSATION

Exhibit 97.1 Adopted Effective October 26, 2023 WINTRUST FINANCIAL CORPORATION POLICY ON RECOUPMENT OF INCENTIVE COMPENSATION Introduction The Board of Directors (the “Board”) of Wintrust Financial Corporation (the “Company”) has adopted this Policy on Recoupment of Incentive Compensation (this “Policy”), which provides for the recoupment of compensation in certain circumstances in the event of a

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

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 001-35077 Wintrust Financial Corporatio

Subsidiaries of the Registrant December 31, 2023 Subsidiary Jurisdiction Barrington Bank & Trust Company, N.A. United States Beverly Bank & Trust Company, N.A. United States Crystal Lake Bank & Trust Company, N.A. United States Chicago Deferred Excha

Exhibit 21.1 Subsidiaries of the Registrant December 31, 2023 Subsidiary Jurisdiction Barrington Bank & Trust Company, N.A. United States Beverly Bank & Trust Company, N.A. United States Crystal Lake Bank & Trust Company, N.A. United States Chicago Deferred Exchange Company, LLC Delaware Elektra Holding Company, LLC Delaware First Insurance Funding of Canada, Inc. Canada FIFC Edge International Co

Exhibit 4.1 of the Registrant’s Annual Report on Form 10-K for the year ended December 31, 2023, filed with the Commission on February 28, 2024

DESCRIPTION OF THE REGISTRANT’S SECURITIES REGISTERED PURSUANT TO SECTION 12 OF THE SECURITIES EXCHANGE ACT OF 1934 Introduction Wintrust Financial Corporation (the “Company,” “we,” “us” or “our”) has three securities registered pursuant to Section 12 of the Securities Exchange Act of 1934: (i) our common stock, (ii) our Fixed-to-Floating Non-Cumulative Perpetual Preferred Stock, Series D, which we refer to as series D preferred, and (iii) depositary shares, each representing a 1/1,000th interest in a share our 6.

WTFC / Wintrust Financial Corporation / VANGUARD GROUP INC - SCHEDULE 13G/A Passive Investment

SC 13G/A 1 tv02291-wintrustfinancialcor.htm SCHEDULE 13G/A SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 (Amendment No.: 12)* Name of issuer: Wintrust Financial Corp Title of Class of Securities: Common Stock CUSIP Number: 97650W108 Date of Event Which Requires Filing of this Statement: December 29, 2023 Check the appropriate box t

Earnings Release Presentation Q4 2023 Wintrust Financial Corporation 22 This document contains forward-looking statements within the meaning of federal securities laws. Forward-looking information can be identified through the use of words such as “i

Earnings Release Presentation Q4 2023 Wintrust Financial Corporation 22 This document contains forward-looking statements within the meaning of federal securities laws.

Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018

Exhibit 99.1 Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018 News Release FOR IMMEDIATE RELEASE January 17, 2024 FOR MORE INFORMATION CONTACT: Timothy S. Crane, President & Chief Executive Officer David A. Dykstra, Vice Chairman & Chief Operating Officer (847) 939-9000 Web site address: www.wintrust.com Wintrust Financial Corporation Reports Record Full Yea

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 17, 2024 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Co

Second Amendment,dated December 11, 2023, to the Amended and Restated Credit Agreement dated December 12, 2022, as amended and restated, among Wintrust Financial Corporation, the lenders named therein, and Wells Fargo Bank, National Association, as administrative agent

EXHIBIT 10.1 EXECUTION VERSION Second Amendment to Amended and Restated Credit Agreement This SECOND AMENDMENT TO AMENDED AND RESTATED CREDIT AGREEMENT (this "Amendment"), dated as of December 11, 2023 (effective as provided herein), is among WINTRUST FINANCIAL CORPORATION, an Illinois corporation ("Borrower"), each lender party hereto (each, a "Lender," and collectively, the "Lenders"), and WELLS

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

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 11, 2023 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (C

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

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 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 OR ☐ 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 001-35077

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 17, 2023 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Co

Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018

Exhibit 99.1 Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018 News Release FOR IMMEDIATE RELEASE October 17, 2023 FOR MORE INFORMATION CONTACT: Timothy S. Crane, President & Chief Executive Officer David A. Dykstra, Vice Chairman & Chief Operating Officer (847) 939-9000 Web site address: www.wintrust.com Wintrust Financial Corporation Reports Record Year-to-

Earnings Release Presentation Q3 2023 Wintrust Financial Corporation 22 This document contains forward-looking statements within the meaning of federal securities laws. Forward-looking information can be identified through the use of words such as “i

Earnings Release Presentation Q3 2023 Wintrust Financial Corporation 22 This document contains forward-looking statements within the meaning of federal securities laws.

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

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 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 OR ☐ 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 001-35077 WINT

Amended and Restated By-laws of Wintrust, as amended (incorporated by reference to Exhibit 3.2 of Wintrust’s Current Report on Form 8-K filed with the Securities and Exchange Commission on August 1, 2023).

EXHIBIT 3.2 Adopted Effective July 27, 2023 AMENDED AND RESTATED BY-LAWS OF WINTRUST FINANCIAL CORPORATION (AN ILLINOIS CORPORATION) AS AMENDED ARTICLE I OFFICES Wintrust Financial Corporation (the “corporation”) shall continuously maintain in the State of Illinois a registered office and a registered agent whose office is identical with such registered office, and may have other offices within or

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): July 27, 2023 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Commi

, among Wintrust Financial Corporation, the lenders named therein, and Wells Fargo Bank, National Association, as administrative agent.

EXECUTION VERSION First Amendment to Amended and Restated Credit Agreement This FIRST AMENDMENT TO AMENDED AND RESTATED CREDIT AGREEMENT (this “Amendment”), dated as of July 17, 2023 (effective as provided herein), is among WINTRUST FINANCIAL CORPORATION, an Illinois corporation (“Borrower”), each Lender a party hereto, and WELLS FARGO BANK, NATIONAL ASSOCIATION, as Administrative Agent (“Administrative Agent”).

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 17, 2023 WINTRUST FINANCIAL

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 17, 2023 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Commi

Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018

Exhibit 99.1 Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018 News Release FOR IMMEDIATE RELEASE July 19, 2023 FOR MORE INFORMATION CONTACT: Timothy S. Crane, President & Chief Executive Officer David A. Dykstra, Vice Chairman & Chief Operating Officer (847) 939-9000 Web site address: www.wintrust.com Wintrust Financial Corporation Reports Record Year-to-Dat

Earnings Release Presentation Q2 2023 Wintrust Financial Corporation 22 This document contains forward-looking statements within the meaning of federal securities laws. Forward-looking information can be identified through the use of words such as “i

a3q2023992earningsreleas Earnings Release Presentation Q2 2023 Wintrust Financial Corporation 22 This document contains forward-looking statements within the meaning of federal securities laws.

by and between First Insurance Funding of Canada Inc. and CIBC Mellon Trust Company, in its capacity as trustee of Plaza Trust, by its Financial Service Agent, Royal Bank of Canada.

EXHIBIT 10.1 ELEVENTH AMENDING AGREEMENT (First Insurance Funding of Canada Inc.) This Eleventh Amending Agreement made as of May 31, 2023. B E T W E E N: FIRST INSURANCE FUNDING OF CANADA INC. (hereinafter referred to as the “Seller” or the “Servicer”) - and - CIBC MELLON TRUST COMPANY, in its capacity as trustee of PLAZA TRUST, (hereinafter referred to as the “Purchaser”) RECITALS: WHEREAS the p

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 31, 2023 WINTRUST FINANCIAL C

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 31, 2023 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Commis

by CIBC Mellon Trust Company, in its capacity as trustee of Plaza Trust, by its Financial Service Agent, Royal Bank of Canada and acknowledged by First Insurance Funding of Canada Inc.

EXHIBIT 10.3 PLAZA TRUST c/o Royal Bank of Canada 200 Bay Street, Royal Bank Plaza 2nd Floor, North Tower Toronto, ON, M5J 2W7 May 31, 2023 First Insurance Funding of Canada Inc. c/o Wintrust Financial Corporation 9700 West Higgins Road, Suite 800 Rosemont, IL 60018 Attention: Mr. David Dykstra, Vice Chairman and Chief Operating Officer Dear Sirs: Receivables Purchase Agreement dated as of Decembe

by Wintrust Financial Corporation in favor of CIBC Mellon Trust Company, Plaza Trust.

EXHIBIT 10.2 Performance Guarantee Confirmation Reference is made to a Performance Guarantee dated as of December 16, 2014 made by the undersigned in favour of the Purchaser (the “Performance Guarantee”). The undersigned acknowledges and confirms that the performance guarantee remains in full force and effect notwithstanding the entering into of this Eleventh Amending Agreement Dated as of the 31s

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 25, 2023 WINTRUST FINANCIAL C

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 25, 2023 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Commis

Restated Certificate of Designations of Wintrust filed on May 5, 2023 with the Secretary of State of the State of Illinois designating the preferences, limitations, voting powers and relative rights of the Series D Preferred Stock (incorporated by reference to Exhibit 3.2 of Wintrust’s Quarterly Report on Form 10-Q for the quarter ended March 31, 2023).

WINTRUST FINANCIAL CORPORATION RESTATED CERTIFICATE OF DESIGNATIONS Pursuant to Section 6.

Filing Fee Table.

Exhibit 107 Calculation of Filing Fee Tables Form S-3 (Form Type) Wintrust Financial Corporation (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered and Carry Forward Securities Security Type Security Class Title (1)(2) Fee Calculation or Carry Forward Rule Amount Registered Proposed Maximum Offering Price Per Unit Maximum Aggregate Offering Price Fee Rate Amount of Re

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

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 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 OR ☐ 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 001-35077 WIN

As filed with the Securities and Exchange Commission on May 9, 2023

TABLE OF CONTENTS As filed with the Securities and Exchange Commission on May 9, 2023 Registration No.

Statement of Eligibility on Form T-1 under the Trust Indenture Act of 1939, as amended, of U.S. Bank Trust Company, National Association, as Trustee.

Exhibit 25.1 SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM T-1 STATEMENT OF ELIGIBILITY UNDER THE TRUST INDENTURE ACT OF 1939 OF A CORPORATION DESIGNATED TO ACT AS TRUSTEE Check if an Application to Determine Eligibility of a Trustee Pursuant to Section 305(b)(2) ¨ U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION (Exact name of Trustee as specified in its charter) 91-1821036 I.R.S. E

Earnings Release Presentation Q1 2023 Wintrust Financial Corporation 2 This document contains forward-looking statements within the meaning of federal securities laws. Forward-looking information can be identified through the use of words such as “in

q12023earningsreleasepre Earnings Release Presentation Q1 2023 Wintrust Financial Corporation 2 This document contains forward-looking statements within the meaning of federal securities laws.

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, 2023 WINTRUST FINANCIAL

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, 2023 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Comm

Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018

Exhibit 99.1 Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018 News Release FOR IMMEDIATE RELEASE April 19, 2023 FOR MORE INFORMATION CONTACT: Edward J. Wehmer, Founder & Chief Executive Officer David A. Dykstra, Vice Chairman & Chief Operating Officer (847) 939-9000 Web site address: www.wintrust.com Wintrust Financial Corporation Reports Record First Quarte

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 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)) ¨ Definitive Proxy Statement x Definitive Additional Materials ¨ Soliciting Material under § 240.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 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)) ☒ Definitive Proxy Statement ☐ Definitive Additional Materials ☐ Soliciting Material under § 240.

Subsidiaries of the Registrant December 31, 2022 Subsidiary Jurisdiction Barrington Bank & Trust Company, N.A. United States Beverly Bank & Trust Company, N.A. United States Crystal Lake Bank & Trust Company, N.A. United States Chicago Deferred Excha

Exhibit 21.1 Subsidiaries of the Registrant December 31, 2022 Subsidiary Jurisdiction Barrington Bank & Trust Company, N.A. United States Beverly Bank & Trust Company, N.A. United States Crystal Lake Bank & Trust Company, N.A. United States Chicago Deferred Exchange Company, LLC Delaware Elektra Holding Company, LLC Delaware First Insurance Funding of Canada, Inc. Canada FIFC Edge International Co

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

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 001-35077 Wintrust Financial Corporatio

DESCRIPTION OF THE REGISTRANT’S SECURITIES REGISTERED PURSUANT TO SECTION 12 OF THE SECURITIES EXCHANGE ACT OF 1934

DESCRIPTION OF THE REGISTRANT’S SECURITIES REGISTERED PURSUANT TO SECTION 12 OF THE SECURITIES EXCHANGE ACT OF 1934 Introduction Wintrust Financial Corporation (the “Company,” “we,” “us” or “our”) has three securities registered pursuant to Section 12 of the Securities Exchange Act of 1934: (i) our common stock, (ii) our Fixed-to-Floating Non-Cumulative Perpetual Preferred Stock, Series D, which we refer to as series D preferred, and (iii) depositary shares, each representing a 1/1,000th interest in a share our 6.

Amended and Restated By-Laws of Wintrust Financial Corporation, Adopted Effective January 26, 2023

Exhibit 3.2 Adopted Effective January 26, 2023 AMENDED AND RESTATED BY-LAWS OF WINTRUST FINANCIAL CORPORATION (AN ILLINOIS CORPORATION) AS AMENDED ARTICLE I OFFICES Wintrust Financial Corporation (the “corporation”) shall continuously maintain in the State of Illinois a registered office and a registered agent whose office is identical with such registered office, and may have other offices within

Amended and Restated Employment Agreement, dated as of January 26, 2023, between the Company and Timothy S. Crane (incorporated by reference to Exhibit 10.1 of the Company's Current Report on Form 8-K filed with the Securities and Exchange Commission on January 30, 2023).*

Exhibit 10.1 AMENDED AND RESTATED EMPLOYMENT AGREEMENT This Amended and Restated Employment Agreement (the “Agreement”) is made by and between WINTRUST FINANCIAL CORPORATION (“Wintrust”), a bank holding company, and Timothy S. Crane, an individual resident in the State of Illinois (“Executive”), as of January 26, 2023. WITNESSETH THAT: WHEREAS, Wintrust and Executive are parties to an Employment A

Amended and Restated Employment Agreement, dated as of January 26, 2023, between the Company and Edward J. Wehmer (incorporated by reference to Exhibit 10.2 of the Company’s Current Report on Form 8-K filed with the Securities and Exchange Commission on January 30, 2023).*

Exhibit 10.2 AMENDED AND RESTATED EMPLOYMENT AGREEMENT This Amended and Restated Employment Agreement (the “Agreement”) is made by and between WINTRUST FINANCIAL CORPORATION (“Wintrust”), a bank holding company, and Edward J. Wehmer, an individual resident in the State of Illinois (“Executive”), as of January 26, 2023. WITNESSETH THAT: WHEREAS, Wintrust and Executive are parties to an Amended and

Regulation FD Disclosure, 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): January 26, 2023 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Co

Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018

Exhibit 99.1 Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018 News Release FOR IMMEDIATE RELEASE January 30, 2023 FOR MORE INFORMATION CONTACT: Edward J. Wehmer, Founder & Chief Executive Officer David A. Dykstra, Vice Chair & Chief Operating Officer (847) 939-9000 Web site address: www.wintrust.com Wintrust To Appoint Timothy S. Crane as Chief Executive Off

Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018

Exhibit 99.1 Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018 News Release FOR IMMEDIATE RELEASE January 18, 2023 FOR MORE INFORMATION CONTACT: Edward J. Wehmer, Founder & Chief Executive Officer David A. Dykstra, Vice Chairman & Chief Operating Officer (847) 939-9000 Web site address: www.wintrust.com Wintrust Financial Corporation Reports Fourth Quarter an

Earnings Release Presentation Q4 2022 Wintrust Financial Corporation 2 This document contains forward-looking statements within the meaning of federal securities laws. Forward-looking information can be identified through the use of words such as “in

Earnings Release Presentation Q4 2022 Wintrust Financial Corporation 2 This document contains forward-looking statements within the meaning of federal securities laws.

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 18, 2023 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Co

WTFC / Wintrust Financial Corp / VANGUARD GROUP INC - SCHEDULE 13G/A Passive Investment

SC 13G/A 1 tv0017-wintrustfinancialcorp.htm SCHEDULE 13G/A SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 (Amendment No.: 11)* Name of issuer: Wintrust Financial Corp. Title of Class of Securities: Common Stock CUSIP Number: 97650W108 Date of Event Which Requires Filing of this Statement: December 30, 2022 Check the appropriate box

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): December 30, 2022 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (C

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

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 12, 2022 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (C

Amended and Restated Credit Agreement, dated as of December 12, 2022, by and among Wintrust Financial Corporation, as Borrower, the lenders who are party to the Agreement and the lenders who may become a party to the Agreement pursuant to terms hereof, as Lenders, and Wells Fargo, National Association, a national banking association, as Administrative Agent for the Lenders.

EXHIBIT 10.1 $300,000,000 AMENDED AND RESTATED CREDIT AGREEMENT dated as of December 12, 2022 by and among WINTRUST FINANCIAL CORPORATION, as Borrower, the Lenders referred to herein, as Lenders, and WELLS FARGO BANK, NATIONAL ASSOCIATION, as Administrative Agent TABLE OF CONTENTS Page ARTICLE I Definitions 1 SECTION 1.1 Definitions 1 SECTION 1.2 Other Interpretive Provisions 25 SECTION 1.3 Accoun

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

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 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 OR ? 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 001-35077

Earnings Release Presentation Q3 2022 Wintrust Financial Corporation 2 This document contains forward-looking statements within the meaning of federal securities laws. Forward-looking information can be identified through the use of words such as “in

Earnings Release Presentation Q3 2022 Wintrust Financial Corporation 2 This document contains forward-looking statements within the meaning of federal securities laws.

Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018

Exhibit 99.1 Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018 News Release FOR IMMEDIATE RELEASE October 18, 2022 FOR MORE INFORMATION CONTACT: Edward J. Wehmer, Founder & Chief Executive Officer David A. Dykstra, Vice Chairman & Chief Operating Officer (847) 939-9000 Web site address: www.wintrust.com Wintrust Financial Corporation Reports Third Quarter 202

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A 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 18, 2022 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (

Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018

Exhibit 99.1 Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018 News Release FOR IMMEDIATE RELEASE October 18, 2022 FOR MORE INFORMATION CONTACT: Edward J. Wehmer, Founder & Chief Executive Officer David A. Dykstra, Vice Chairman & Chief Operating Officer (847) 939-9000 Web site address: www.wintrust.com Wintrust Financial Corporation Reports Third Quarter 202

Earnings Release Presentation Q3 2022 Wintrust Financial Corporation 2 This document contains forward-looking statements within the meaning of federal securities laws. Forward-looking information can be identified through the use of words such as “in

Earnings Release Presentation Q3 2022 Wintrust Financial Corporation 2 This document contains forward-looking statements within the meaning of federal securities laws.

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 18, 2022 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Co

Fifth Amendment, dated as of September 13, 2022, to the Credit Agreement dated as of September 18, 2018, as amended, among Wintrust Financial Corporation, the lenders named therein, and Wells Fargo Bank, National Association, as administrative agent

EXHIBIT 10.1 Fifth Amendment to Credit Agreement This FIFTH AMENDMENT TO CREDIT AGREEMENT (this "Amendment"), dated as of September 13, 2022 (effective as provided herein), is among WINTRUST FINANCIAL CORPORATION, an Illinois corporation ("Borrower"), each Lender a party hereto, and WELLS FARGO BANK, NATIONAL ASSOCIATION, as Administrative Agent ("Administrative Agent"). RECITALS: Borrower, Lender

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

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): September 13, 2022 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (

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

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 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 OR ? 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 001-35077 WINT

Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018

Exhibit 99.1 Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018 News Release FOR IMMEDIATE RELEASE July 20, 2022 FOR MORE INFORMATION CONTACT: Edward J. Wehmer, Founder & Chief Executive Officer David A. Dykstra, Vice Chairman & Chief Operating Officer (847) 939-9000 Web site address: www.wintrust.com Wintrust Financial Corporation Reports Second Quarter 2022

Second Quarter 2022 Earnings Release Presentation dated July 20, 2022

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 20, 2022 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Commi

Underwriting Agreement, dated as of June 7, 2022, between Wintrust Financial Corporation and RBC Capital Markets, LLC, as representative of the several underwriters named therein

Exhibit?1.1 ? EXECUTION COPY ? WINTRUST FINANCIAL CORPORATION ? (an Illinois corporation) ? 3,000,000 Shares of Common Stock ? UNDERWRITING AGREEMENT ? Dated: June?7, 2022 ? ? ? WINTRUST FINANCIAL CORPORATION ? (an Illinois corporation) ? 3,000,000 Shares of Common Stock ? UNDERWRITING AGREEMENT ? June?7, 2022 ? RBC Capital Markets, LLC as Representative of the several Underwriters ? c/o RBC Capit

Entry into a Material Definitive Agreement, 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): June 7, 2022 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Commis

3,000,000 Shares Wintrust Financial Corporation Common Stock

TABLE OF CONTENTS ?Filed Pursuant to Rule 424(b)(5)? ?File No. 333-238023? PROSPECTUS SUPPLEMENT (To prospectus dated May 6, 2020) 3,000,000 Shares Wintrust Financial Corporation Common Stock We are offering 3,000,000 shares of our common stock. Our common stock is listed on the Nasdaq Global Select Market under the symbol ?WTFC.? On June 7, 2022, the last sale price of the shares as reported on t

Calculation of Filing Fee Table

Exhibit ? Filing Fees Calculation of Filing Fee Table 424(b)(5) (Form Type) Wintrust Financial Corporation (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered Securities Security Type Security Class Title Fee Calculation or Carry Forward Rule Amount Registered Proposed Maximum Offering Price Per Unit Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee(1) Fees to Be Paid Equity Common stock, no par value per share 457(r) 3,450,000 (2) $ 86.

Subject to Completion Preliminary Prospectus Supplement dated June 7, 2022

TABLE OF CONTENTS The information in this preliminary prospectus supplement is not complete and may be changed.

Wintrust Financial Corporation 2022 Stock Incentive Plan

EXHIBIT 10.1 WINTRUST FINANCIAL CORPORATION 2022 STOCK INCENTIVE PLAN 1.Purpose; Effect on Predecessor Plan. The purpose of the Wintrust Financial Corporation 2022 Stock Incentive Plan is to benefit the Corporation and its Subsidiaries by enabling the Corporation to offer certain present and future officers, employees, directors and consultants stock-based incentives and other equity interests in

As filed with the Securities and Exchange Commission on May 27, 2022

As filed with the Securities and Exchange Commission on May 27, 2022 Registration No.

Filing Fee Table.

EXHIBIT 107 Calculation of Filing Fee Table FORM S-8 (Form Type) Wintrust Financial Corporation (Exact Name of Registrant as Specified in its Charter) Newly Registered Securities Security Type Security Class Title Fee Calculation Rule Amount Registered(1) Proposed Maximum Offering Price Per Unit(2) Maximum Aggregate Offering Price(2) Fee Rate Amount of Registration Fee(2) Equity(3) Common Stock, no par value per share Rule 457(c) and Rule 457(h) 1,584,727 $ 81.

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits, 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): May 26, 2022 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Commis

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

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 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 OR ? 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 001-35077 WIN

by Wintrust Financial Corporation in favor of CIBC Mellon Trust Company, Plaza Trust.

EXHIBIT 10.2 Performance Guarantee Confirmation Reference is made to a Performance Guarantee dated as of December 16, 2014 made by the undersigned in favour of the Purchaser (the ?Performance Guarantee?). The undersigned acknowledges and confirms that the performance guarantee remains in full force and effect notwithstanding the entering into of this Tenth Amending Agreement Dated as of the 2nd da

by and between First Insurance Funding of Canada Inc. and CIBC Mellon Trust Company, in its capacity as trustee of Plaza Trust, by its Financial Service Agent, Royal Bank of Canada.

EXHIBIT 10.1 TENTH AMENDING AGREEMENT (First Insurance Funding of Canada Inc.) This Tenth Amending Agreement made as of May 2, 2022. B E T W E E N: FIRST INSURANCE FUNDING OF CANADA INC. (hereinafter referred to as the ?Seller? or the ?Servicer?) - and - CIBC MELLON TRUST COMPANY, in its capacity as trustee of PLAZA TRUST, (hereinafter referred to as the ?Purchaser?) RECITALS: WHEREAS the parties

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

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 2, 2022 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Commiss

by CIBC Mellon Trust Company, in its capacity as trustee of Plaza Trust, by its Financial Service Agent, Royal Bank of Canada and acknowledged by First Insurance Funding of Canada Inc.

EXHIBIT 10.3 PLAZA TRUST c/o Royal Bank of Canada 200 Bay Street, Royal Bank Plaza 2nd Floor, North Tower Toronto, ON, M5J 2W7 May 2, 2022 First Insurance Funding of Canada Inc. c/o Wintrust Financial Corporation 9700 West Higgins Road, Suite 800 Rosemont, IL 60018 Attention: Mr. David Dykstra, Vice Chairman and Chief Operating Officer Dear Sirs: Receivables Purchase Agreement dated as of December

Earnings Release Presentation Q1 2022 Wintrust Financial Corporation 2 This document contains forward-looking statements within the meaning of federal securities laws. Forward-looking information can be identified through the use of words such as “in

a1q22earningsreleasepres Earnings Release Presentation Q1 2022 Wintrust Financial Corporation 2 This document contains forward-looking statements within the meaning of federal securities laws.

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 19, 2022 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Comm

Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018

Exhibit 99.1 Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018 News Release FOR IMMEDIATE RELEASE April 19, 2022 FOR MORE INFORMATION CONTACT: Edward J. Wehmer, Founder & Chief Executive Officer David A. Dykstra, Vice Chairman & Chief Operating Officer (847) 939-9000 Web site address: www.wintrust.com Wintrust Financial Corporation Reports First Quarter 2022

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 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)) ? Definitive Proxy Statement ? Definitive Additional Materials ? Soliciting Material under ? 240.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 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)) ? Definitive Proxy Statement ? Definitive Additional Materials ? Soliciting Material under ? 240.

Subsidiaries of the Registrant December 31, 2021 Subsidiary Jurisdiction Barrington Bank & Trust Company, N.A. United States Beverly Bank & Trust Company, N.A. United States Crystal Lake Bank & Trust Company, N.A. United States Chicago Deferred Excha

Exhibit 21.1 Subsidiaries of the Registrant December 31, 2021 Subsidiary Jurisdiction Barrington Bank & Trust Company, N.A. United States Beverly Bank & Trust Company, N.A. United States Crystal Lake Bank & Trust Company, N.A. United States Chicago Deferred Exchange Company, LLC Delaware Elektra Holding Company, LLC Delaware First Insurance Funding of Canada, Inc. Canada FIFC Edge International Co

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

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, 2021 ? 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 001-35077 Wintrust Financial Corporatio

WTFC / Wintrust Financial Corp / 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.: 10)* Name of issuer: Wintrust Financial Corp. Title of Class of Securities: Common Stock CUSIP Number: 97650W108 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 fi

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): January 27, 2022 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Co

dopted Effective January 27, 2022

Adopted Effective January 27, 2022 AMENDED AND RESTATED BY-LAWS OF WINTRUST FINANCIAL CORPORATION (AN ILLINOIS CORPORATION) AS AMENDED ARTICLE I OFFICES Wintrust Financial Corporation (the ?corporation?) shall continuously maintain in the State of Illinois a registered office and a registered agent whose office is identical with such registered office, and may have other offices within or without the state.

Earnings Release Presentation Q4 2021 Wintrust Financial Corporation 2 Celebrated Wintrust’s 30th anniversary by reporting record annual net income and eclipsing $50 billion in total assets. The fourth quarter of 2021 was characterized by significant

Earnings Release Presentation Q4 2021 Wintrust Financial Corporation 2 Celebrated Wintrust?s 30th anniversary by reporting record annual net income and eclipsing $50 billion in total assets.

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 19, 2022 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Co

Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018

Exhibit 99.1 Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018 News Release FOR IMMEDIATE RELEASE January 19, 2022 FOR MORE INFORMATION CONTACT: Edward J. Wehmer, Founder & Chief Executive Officer David A. Dykstra, Vice Chairman & Chief Operating Officer (847) 939-9000 Web site address: www.wintrust.com Wintrust Financial Corporation Reports Fourth Quarter 20

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

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 23, 2021 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (C

Fourth Amendment, dated as of December 23, 2021, to the Credit Agreement dated as of September 18, 2018, as amended, among Wintrust Financial Corporation, the lenders named therein, and Wells Fargo Bank, National Association, as administrative agent.

EXHIBIT 10.1 Fourth Amendment to Credit Agreement This FOURTH AMENDMENT TO CREDIT AGREEMENT (this "Amendment"), dated as of December 23, 2021 (effective as provided herein), is among WINTRUST FINANCIAL CORPORATION, an Illinois corporation ("Borrower"), each Lender a party hereto, and WELLS FARGO BANK, NATIONAL ASSOCIATION, as Administrative Agent ("Administrative Agent"). RECITALS: Borrower, Lende

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

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 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 OR ? 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 001-35077

Entry into a Material Definitive Agreement, 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 28, 2021 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Co

Wintrust Financial Corporation 9700 West Higgins Road, Rosemont, Illinois 60018

EXHIBIT 99.1 Wintrust Financial Corporation 9700 West Higgins Road, Rosemont, Illinois 60018 News Release FOR IMMEDIATE RELEASE October 28, 2021 FOR MORE INFORMATION CONTACT: Edward J. Wehmer, Founder & Chief Executive Officer David A. Dykstra, Vice Chairman & Chief Operating Officer (847) 939-9000 Website address: www.wintrust.com WINTRUST FINANCIAL CORPORATION ANNOUNCES CASH DIVIDENDS AND NEW SH

Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018

Exhibit 99.1 Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018 News Release FOR IMMEDIATE RELEASE October 19, 2021 FOR MORE INFORMATION CONTACT: Edward J. Wehmer, Founder & Chief Executive Officer David A. Dykstra, Vice Chairman & Chief Operating Officer (847) 939-9000 Web site address: www.wintrust.com Wintrust Financial Corporation Reports Third Quarter 202

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, 2021 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Co

Earnings Release Presentation Q3 2021 Wintrust Financial Corporation 2 Our core fundamentals were strong, with robust loan and deposit growth, increased net interest income despite significant PPP loan reductions, record wealth management revenue, st

Earnings Release Presentation Q3 2021 Wintrust Financial Corporation 2 Our core fundamentals were strong, with robust loan and deposit growth, increased net interest income despite significant PPP loan reductions, record wealth management revenue, strong mortgage revenues, improved net overhead and efficiency ratios compared to the prior quarter, strong loan pipelines and very good credit quality metrics.

Third Amendment, dated as of September 14, 2021, to the Credit Agreement dated as of September 18, 2018, as amended, among Wintrust Financial Corporation, the lenders named therein, and Wells Fargo Bank, National Association, as administrative agent.

EXHIBIT 10.1 Execution Version Third Amendment to Credit Agreement This THIRD AMENDMENT TO CREDIT AGREEMENT (this "Amendment"), dated as of September 14, 2021 (effective as provided herein), is among WINTRUST FINANCIAL CORPORATION, an Illinois corporation ("Borrower"), each Lender a party hereto, and WELLS FARGO BANK, NATIONAL ASSOCIATION, as Administrative Agent ("Administrative Agent"). RECITALS

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

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): September 14, 2021 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (

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

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 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 OR ? 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 001-35077 WINT

Earnings Release Presentation Q2 2021 Wintrust Financial Corporation 2 ROA3 • Total loans, excluding Paycheck Protection Program ("PPP") loans, increased by $1.2 billion or 15%, on an annualized basis. • Total deposits increased by $932 million. • Ne

Earnings Release Presentation Q2 2021 Wintrust Financial Corporation 2 ROA3 ? Total loans, excluding Paycheck Protection Program ("PPP") loans, increased by $1.

Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018

Exhibit 99.1 Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018 News Release FOR IMMEDIATE RELEASE July 19, 2021 FOR MORE INFORMATION CONTACT: Edward J. Wehmer, Founder & Chief Executive Officer David A. Dykstra, Vice Chairman & Chief Operating Officer (847) 939-9000 Web site address: www.wintrust.com Wintrust Financial Corporation Reports Second Quarter 2021

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 19, 2021 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Commi

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): May 27, 2021 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Commis

As filed with the Securities and Exchange Commission on May 27, 2021

As filed with the Securities and Exchange Commission on May 27, 2021 Registration No.

Form of Restricted Share Unit Award Agreement under the Company’s 2015 Stock Incentive Plan.*

WINTRUST FINANCIAL CORPORATION RESTRICTED SHARE UNIT AWARD AGREEMENT This Restricted Share Unit Award Agreement (herein called the "Agreement") is made and entered into as of January 28, 2021 by and between Wintrust Financial Corporation, an Illinois corporation (the "Company"), and First Name Last Name ("Employee").

Form of Performance Award Agreement - Share Settled under the Company’s 2015 Stock Incentive Plan.*

WINTRUST FINANCIAL CORPORATION PERFORMANCE AWARD AGREEMENT This Performance Award Agreement (the ?Agreement?) is dated as of January 28, 2021 (the ?Grant Date?), by and between Wintrust Financial Corporation, an Illinois corporation (the ?Company?), and First Name Last Name (the ?Participant?) and is governed by the terms of the Wintrust Financial Corporation Long-Term Incentive Program (the ?Program?), which was adopted by the Compensation Committee (the ?Committee?) of the Board of Directors of the Company under the Wintrust Financial Corporation 2015 Stock Incentive Plan (the ?Plan?).

Quarterly Report - 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 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 OR ? 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 001-35077 WIN

Earnings Release Presentation Q1 2021 Wintrust Financial Corporation 2 ROA3 • Total loans, excluding Paycheck Protection Program ("PPP") loans, increased by $515 million. • Total investment securities increased by $1.0 billion as the Company deployed

Earnings Release Presentation Q1 2021 Wintrust Financial Corporation 2 ROA3 ? Total loans, excluding Paycheck Protection Program ("PPP") loans, increased by $515 million.

Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018

Exhibit 99.1 Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018 News Release FOR IMMEDIATE RELEASE April 19, 2021 FOR MORE INFORMATION CONTACT: Edward J. Wehmer, Founder & Chief Executive Officer David A. Dykstra, Vice Chairman & Chief Operating Officer (847) 939-9000 Web site address: www.wintrust.com Wintrust Financial Corporation Reports Record First Quarte

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 19, 2021 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Comm

Amended and Restated By-laws

EX-3.2 2 amendedandrestatedbylawsas.htm EX-3.2 AMENDED AND RESTATED BY-LAWS AMENDED AND RESTATED BY-LAWS OF WINTRUST FINANCIAL CORPORATION (AN ILLINOIS CORPORATION) AS AMENDED ARTICLE I OFFICES Wintrust Financial Corporation (the “corporation”) shall continuously maintain in the State of Illinois a registered office and a registered agent whose office is identical with such registered office, and

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): April 6, 2021 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Commi

- DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 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)) ? Definitive Proxy Statement ? Definitive Additional Materials ? Soliciting Material under ? 240.

- DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 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)) ? Definitive Proxy Statement ? Definitive Additional Materials ? Soliciting Material under ? 240.

Subsidiaries of the Registrant December 31, 2020 Subsidiary Jurisdiction Barrington Bank & Trust Company, N.A. United States Beverly Bank & Trust Company, N.A. United States Crystal Lake Bank & Trust Company, N.A. United States Chicago Deferred Excha

EX-21.1 3 exhibit211subsidiaries1231.htm EX-21.1 Exhibit 21.1 Subsidiaries of the Registrant December 31, 2020 Subsidiary Jurisdiction Barrington Bank & Trust Company, N.A. United States Beverly Bank & Trust Company, N.A. United States Crystal Lake Bank & Trust Company, N.A. United States Chicago Deferred Exchange Company, LLC Delaware Elektra Holding Company, LLC Delaware First Insurance Funding

Annual Report - 10-K

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, 2020 ? 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 001-35077 Wintrust Financial Corporatio

DESCRIPTION OF THE REGISTRANT’S SECURITIES REGISTERED PURSUANT TO SECTION 12 OF THE SECURITIES EXCHANGE ACT OF 1934

EX-4.1 2 exhibit41registrantsecurit.htm EX-4.1 DESCRIPTION OF THE REGISTRANT’S SECURITIES REGISTERED PURSUANT TO SECTION 12 OF THE SECURITIES EXCHANGE ACT OF 1934 Introduction Wintrust Financial Corporation (the “Company,” “we,” “us” or “our”) has three securities registered pursuant to Section 12 of the Securities Exchange Act of 1934: (i) our common stock, (ii) our Fixed-to-Floating Non-Cumulati

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 (Amendment No.: 9)*

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 (Amendment No.: 9)* Name of issuer: Wintrust Financial Corp. Title of Class of Securities: Common Stock CUSIP Number: 97650W108 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 fil

Earnings Release Presentation Q4 2020 Wintrust Financial Corporation 2 ROA3 • Total loans, excluding Paycheck Protection Program ("PPP") loans, increased by $607 million primarily due to growth in commercial loans and life insurance premium finance r

q42020earningspresentati Earnings Release Presentation Q4 2020 Wintrust Financial Corporation 2 ROA3 • Total loans, excluding Paycheck Protection Program ("PPP") loans, increased by $607 million primarily due to growth in commercial loans and life insurance premium finance receivables.

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): January 20, 2021 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Co

Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018

Exhibit 99.1 Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018 News Release FOR IMMEDIATE RELEASE January 20, 2021 FOR MORE INFORMATION CONTACT: Edward J. Wehmer, Founder & Chief Executive Officer David A. Dykstra, Vice Chairman & Chief Operating Officer (847) 939-9000 Web site address: www.wintrust.com Wintrust Financial Corporation Reports Fourth Quarter 20

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

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, 2021 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Co

, in its capacity as trustee of Plaza Trust, by its Financial Service Agent, Royal Bank of Canada.

EX-10.1 2 ex101ninthamendingagreemen.htm EX-10.1 NINTH AMENDING AGREEMENT EXHIBIT 10.1 NINTH AMENDING AGREEMENT (First Insurance Funding of Canada Inc.) This Ninth Amending Agreement made as of January 15, 2021. B E T W E E N: FIRST INSURANCE FUNDING OF CANADA INC. (hereinafter referred to as the “Seller” or the “Servicer”) - and - CIBC MELLON TRUST COMPANY, in its capacity as trustee of PLAZA TRU

, in its capacity as trustee of Plaza Trust, by its Financial Service Agent, Royal Bank of Canada and acknowledged by First Insurance Funding of Canada Inc.

EX-10.3 4 ex103firstinsurancefeelett.htm EX-10.3 FEE LETTER EXHIBIT 10.3 PLAZA TRUST c/o Royal Bank of Canada 200 Bay Street, Royal Bank Plaza 2nd Floor, North Tower Toronto, ON, M5J 2W7 January 15, 2021 First Insurance Funding of Canada Inc. c/o Wintrust Financial Corporation 9700 West Higgins Road, Suite 800 Rosemont, IL 60018 Attention: Mr. David Dykstra, Vice Chairman and Chief Operating Offic

by Wintrust Financial Corporation in favor of CIBC Mellon Trust Company, Plaza Trust.

EX-10.2 3 ex102performanceguaranteec.htm EX-10.2 PERFORMANCE GUARANTEE EXHIBIT 10.2 Performance Guarantee Confirmation Reference is made to a Performance Guarantee dated as of December 16, 2014 made by the undersigned in favour of the Purchaser (the “Performance Guarantee”). The undersigned acknowledges and confirms that the performance guarantee remains in full force and effect notwithstanding th

- FORM S-8

As filed with the Securities and Exchange Commission on November 6, 2020 Registration No.

Quarterly Report - 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 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 OR ☐ 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 001-35077

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 21, 2020 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Co

Wintrust Financial Corporation Earnings Release Presentation Q3 2020 Q3 2020 Highlights Performance Highlights vs. Q2 2020 Third Quarter 2020 Highlights as compared to Second Quarter 2020 (Q3 2020) • Loan growth of $733 million or 9%, on an annualize

earningsreleasepresent20 Wintrust Financial Corporation Earnings Release Presentation Q3 2020 Q3 2020 Highlights Performance Highlights vs.

Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018

Exhibit 99.1 Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018 News Release FOR IMMEDIATE RELEASE October 21, 2020 FOR MORE INFORMATION CONTACT: Edward J. Wehmer, Founder & Chief Executive Officer David A. Dykstra, Vice Chairman & Chief Operating Officer (847) 939-9000 Web site address: www.wintrust.com Wintrust Financial Corporation Reports Record Third Quar

Second Amendment, dated as of September 15, 2020, to the Credit Agreement dated as of September 18, 2018, as amended, among Wintrust Financial Corporation, the lenders named therein, and Wells Fargo Bank, National Association, as administrative agent.

EXHIBIT 10.1 EXECUTION VERSION SECOND AMENDMENT TO CREDIT AGREEMENT This SECOND AMENDMENT TO CREDIT AGREEMENT (this "Amendment"), dated as of September 15, 2020 (effective as provided herein), is among WINTRUST FINANCIAL CORPORATION, an Illinois corporation ("Borrower"), each Lender a party hereto, and WELLS FARGO BANK, NATIONAL ASSOCIATION, as Administrative Agent ("Administrative Agent"). RECITA

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 - 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): September 15, 2020 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (

Quarterly Report - 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 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 OR ☐ 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 001-35077 WINT

Wintrust Financial Corporation Earnings Release Presentation Q2 2020 Q2 2020 Highlights Performance Highlights vs. Q1 2020 Second Quarter 2020 Highlights as compared to First Quarter 2020 (Q2 2020) • Net interest income increased by $1.7 million comp

EX-99.2 3 q22020earningspresent.htm EXHIBIT 99.2 Wintrust Financial Corporation Earnings Release Presentation Q2 2020 Q2 2020 Highlights Performance Highlights vs. Q1 2020 Second Quarter 2020 Highlights as compared to First Quarter 2020 (Q2 2020) • Net interest income increased by $1.7 million compared to the first quarter of 2020 as the impact of a $5.1 billion increase in average earning assets

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, 2020 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Commi

Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018

Exhibit 99.1 Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018 News Release FOR IMMEDIATE RELEASE July 21, 2020 FOR MORE INFORMATION CONTACT: Edward J. Wehmer, Founder & Chief Executive Officer David A. Dykstra, Vice Chairman & Chief Operating Officer (847) 939-9000 Web site address: www.wintrust.com Wintrust Financial Corporation Reports Second Quarter 2020

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): May 28, 2020 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Commis

- 8-A12B

8-A12B 1 a20-2118018a12b.htm 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 12(g) OF THE SECURITIES EXCHANGE ACT OF 1934 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 36-3873352 (State of incorporation or organization) (I.R.S. Empl

Eighth Amending Agreement, dated as of May 20, 2020 by and between First Insurance Funding of Canada Inc. and CIBC Mellon Trust, in its capacity as trustee of Plaza Trust, by its Financial Service Agent, Royal Bank of Canada.

EXHIBIT 10.1 EIGHTH AMENDING AGREEMENT (First Insurance Funding of Canada Inc.) This Eighth Amending Agreement made as of May 20, 2020. B E T W E E N: FIRST INSURANCE FUNDING OF CANADA INC. (hereinafter referred to as the “Seller” or the “Servicer”) - and - CIBC MELLON TRUST COMPANY, in its capacity as trustee of PLAZA TRUST, (hereinafter referred to as the “Purchaser”) RECITALS: WHEREAS the parti

Performance Guarantee Confirmation, made as of May 20, 2020, by the Company in favor of CIBC Mellon Trust Company, in its capacity as trustee of PLAZA Trust (incorporated by reference to Exhibit 10.2 of the Company’s Current Report on Form 8-K filed with the Securities and Exchange Commission on May 26, 2020).

EXHIBIT 10.2 Performance Guarantee Confirmation Reference is made to a Performance Guarantee dated as of December 16, 2014 made by the undersigned in favour of the Purchaser (the “Performance Guarantee”). The undersigned acknowledges and confirms that the performance guarantee remains in full force and effect notwithstanding the entering into of this eighth amendment. Dated as of the 20th day of M

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

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 20, 2020 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Commis

Fee Letter dated as of May 20, 2020 by CIBC Mellon Trust, in its capacity as trustee of Plaza Trust, by its Financial Service Agent, Royal Bank of Canada and acknowledged by First Insurance Funding of Canada Inc.

EXHIBIT 10.3 PLAZA TRUST c/o Royal Bank of Canada 200 Bay Street, Royal Bank Plaza 2nd Floor, North Tower Toronto, ON, M5J 2W7 May 20, 2020 First Insurance Funding of Canada Inc. c/o Wintrust Financial Corporation 9700 West Higgins Road, Suite 800 Rosemont, IL 60018 Attention: Mr. David Dykstra, Vice Chairman and Chief Operating Officer Dear Sirs: Receivables Purchase Agreement dated as of Decembe

Material Modification to Rights of Security Holders, 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): May 15, 2020 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois (State or other jurisdiction of Incorporation) 001-35077 (Commission File N

Deposit Agreement, by and among the Company, U.S. Bank National Association, as registrar and as depositary, and the holders from time to time of the depositary receipts described therein (incorporated by reference to Exhibit 4.1 of the Company’s Current Report on Form 8-K filed with the Securities and Exchange Commission on May 15, 2020).

Exhibit 4.2 EXECUTION VERSION DEPOSIT AGREEMENT among Wintrust Financial Corporation, as Issuer U.S. Bank National Association, as Depositary, and THE HOLDERS FROM TIME TO TIME OF THE DEPOSITARY RECEIPTS DESCRIBED HEREIN Dated as of May 15, 2020 TABLE OF CONTENTS Page ARTICLE I DEFINED TERMS 1 Section 1.1. Definitions. 1 ARTICLE II FORM OF RECEIPTS, DEPOSIT OF STOCK, EXECUTION AND DELIVERY, TRANSF

Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Entry into a Material Definitive Agreement, Material Modification to Rights 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): May 6, 2020 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois (State or other jurisdiction of Incorporation) 001-35077 (Commission File Nu

Underwriting Agreement, dated as of May 6, 2020, between Wintrust Financial Corporation and RBC Capital Markets, LLC, as representative of the several underwriters named in Schedule A thereto.

Exhibit 1.1 Execution Version WINTRUST FINANCIAL CORPORATION (an Illinois corporation) 10,000,000 Depositary Shares, Each Representing a 1/1000th Interest in a Share of 6.875% Fixed Rate Reset Non-Cumulative Perpetual Preferred Stock, Series E UNDERWRITING AGREEMENT Dated: May 6, 2020 WINTRUST FINANCIAL CORPORATION (an Illinois corporation) 10,000,000 Depositary Shares, Each Representing a 1/1000t

Certificate of Designations of the Company filed on May 7, 2020 with the Secretary of State of the State of Illinois designating the preferences, limitations, voting powers and relative rights of the Series E Preferred Stock (incorporated by reference to Exhibit 3.1 of the Company’s Current Report on Form 8-K filed with the Securities and Exchange Commission on May 8, 2020).

Exhibit 3.1 WINTRUST FINANCIAL CORPORATION CERTIFICATE OF DESIGNATIONS Pursuant to Section 6.10 of the Illinois Business Corporation Act 6.875% FIXED-RATE RESET NON-CUMULATIVE PERPETUAL PREFERRED STOCK, SERIES E (no par value per share) The undersigned, David A. Dykstra, Vice Chairman and Chief Operating Officer of Wintrust Financial Corporation, an Illinois corporation (the “Corporation”), hereby

CALCULATION OF REGISTRATION FEE Title of Each Class of Securities to be Registered Maximum Aggregate Offering Price Amount of Registration Fee(1) Depositary Shares of Wintrust Financial Corporation (each representing a 1/1,000th interest in a share o

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

WINTRUST FINANCIAL CORPORATION 10,000,000 DEPOSITARY SHARES, EACH REPRESENTING A 1/1,000th INTEREST IN A SHARE OF 6.875% FIXED-RATE RESET NON-CUMULATIVE PERPETUAL PREFERRED STOCK, SERIES E (liquidation preference $25,000 per share (equivalent to $25.

FWP 1 a20-184464fwp.htm FWP Filed pursuant to Rule 433 Issuer Free Writing Prospectus, dated May 6, 2020 Supplementing the Preliminary Prospectus Supplement, dated May 6, 2020 Registration No. 333-238023 WINTRUST FINANCIAL CORPORATION 10,000,000 DEPOSITARY SHARES, EACH REPRESENTING A 1/1,000th INTEREST IN A SHARE OF 6.875% FIXED-RATE RESET NON-CUMULATIVE PERPETUAL PREFERRED STOCK, SERIES E (liquid

- S-3ASR

Use these links to rapidly review the document TABLE OF CONTENTS Table of Contents As filed with the Securities and Exchange Commission on May 6, 2020 Registration No.

Subject to Completion Preliminary Prospectus Supplement dated May 6, 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.

Form of Subordinated Indenture

Exhibit 4.5 WINTRUST FINANCIAL CORPORATION as the Company and U.S. BANK NATIONAL ASSOCIATION as Trustee Subordinated Indenture Dated as of CROSS-REFERENCE TABLE Trust Indenture Act Section Indenture Section 310(a)(1) 7.11 (a)(2) 7.11 (a)(3) N.A. (a)(4) N.A. (a)(5) 7.08; 7.11 (b) 7.08; 7.09; 7.11; 10.02 311(a) 7.03 (b) 7.03 312(a) 4.03 (b) 10.15 (c) 10.15 313(a) 7.06 (b)(1) 7.06 (b)(2) 7.06 (c) 7.0

Statement of Eligibility on Form T-1 under the Trust Indenture Act of 1939, as amended, of U.S. Bank National Association, as Trustee.

Exhibit 25.1 SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM T-1 STATEMENT OF ELIGIBILITY UNDER THE TRUST INDENTURE ACT OF 1939 OF A CORPORATION DESIGNATED TO ACT AS TRUSTEE Check if an Application to Determine Eligibility of a Trustee Pursuant to Section 305(b)(2) o U.S. BANK NATIONAL ASSOCIATION (Exact name of Trustee as specified in its charter) 31-0841368 I.R.S. Employer Identif

Quarterly Report - 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 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 OR ☐ 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 001-35077 WIN

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, 2020 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Comm

Wintrust Financial Corporation Earnings Release Presentation Q1 2020 Q1 2020 Highlights Performance Highlights vs. Q4 2019 Key Observations (Q1 2020) • Net interest income decreased by $436,000 compared to the fourth quarter of 2019 as the impact of

earningsreleasepresent20 Wintrust Financial Corporation Earnings Release Presentation Q1 2020 Q1 2020 Highlights Performance Highlights vs.

Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018

Exhibit 99.1 Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018 News Release FOR IMMEDIATE RELEASE April 21, 2020 FOR MORE INFORMATION CONTACT: Edward J. Wehmer, Founder & Chief Executive Officer David A. Dykstra, Vice Chairman & Chief Operating Officer (847) 939-9000 Web site address: www.wintrust.com Wintrust Financial Corporation Reports First Quarter 2020

Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018

EXHIBIT 99.1 Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018 News Release FOR IMMEDIATE RELEASE April 17, 2020 FOR MORE INFORMATION CONTACT: Edward J. Wehmer, Founder & Chief Executive Officer David A. Dykstra, Vice Chairman & Chief Operating Officer (847) 939-9000 Web site address: www.wintrust.com Wintrust Financial Corporation to Make Loans to Approximat

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): April 17, 2020 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Comm

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): April 10, 2020 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Comm

Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018

EXHIBIT 99.1 Wintrust Financial Corporation 9700 W. Higgins Road, Suite 800, Rosemont, Illinois 60018 News Release FOR IMMEDIATE RELEASE April 10, 2020 FOR MORE INFORMATION CONTACT: Edward J. Wehmer, Founder & Chief Executive Officer David A. Dykstra, Vice Chairman & Chief Operating Officer (847) 939-9000 Web site address: www.wintrust.com Wintrust Financial Corporation Working Tirelessly To Suppo

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): April 7, 2020 WINTRUST FINANCIAL CORPORATION (Exact name of registrant as specified in its charter) Illinois 001-35077 36-3873352 (State or other jurisdiction of Incorporation) (Commi

Amended and Restated Bylaws of the Company (incorporated by reference to Exhibit 3.2 to the Company’s Current Report on Form 8-K, filed with the Securities and Exchange Commission on April 13, 2020, and incorporated herein by reference).

EX-3.2 2 wintrustfinancialamend.htm EXHIBIT 3.2 AMENDED AND RESTATED BY-LAWS OF WINTRUST FINANCIAL CORPORATION Exhibit 3.2 AMENDED AND RESTATED BY-LAWS OF WINTRUST FINANCIAL CORPORATION (AN ILLINOIS CORPORATION) AS AMENDED ARTICLE I OFFICES Wintrust Financial Corporation (the “corporation”) shall continuously maintain in the State of Illinois a registered office and a registered agent whose office

Definitive Proxy Statement on Schedule 14A filed with the SEC on April 9, 2020

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 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)) ☒ Definitive Proxy Statement ☐ Definitive Additional Materials ☐ Soliciting Material under § 240.

WTFC / Wintrust Financial Corp. DEFA14A - - DEFA14A

DEFA14A 1 tm2015078-2defa14a.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 o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (