Results of Operations and Financial Condition The information in this Current Report is being furnished and shall not be deemed “filed” for the purposes of Section 18 of the Securities Exchange Act of 1934, as amended, or otherwise subject to the liabilities of that Section. The information in this Current Report shall not be incorporated by reference into any registration statement or other document pursuant to the Securities Act of 1933, as amended. On July 20, 2026, Wintrust Financial Corp…

Results of Operations and Financial Condition The information in this Current Report is being furnished and shall not be deemed “filed” for the purposes of Section 18 of the Securities Exchange Act of 1934, as amended, or otherwise subject to the liabilities of that Section. The information in this Current Report shall not be incorporated by reference into any registration statement or other document pursuant to the Securities Act of 1933, as amended. On April 20, 2026, Wintrust Financial Cor…

Results of Operations and Financial Condition The information in this Current Report is being furnished and shall not be deemed “filed” for the purposes of Section 18 of the Securities Exchange Act of 1934, as amended, or otherwise subject to the liabilities of that Section. The information in this Current Report shall not be incorporated by reference into any registration statement or other document pursuant to the Securities Act of 1933, as amended. On January 20, 2026, Wintrust Financial C…

Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant. The information provided in

Entry into a Material Definitive Agreement. On December 15, 2025, an indirect subsidiary of Wintrust Financial Corporation (“Wintrust”), First Insurance Funding of Canada Inc. (“First Canada) entered into the Thirteenth Amending Agreement, dated as of December 15, 2025 (the “Amendment”) to the Receivables Purchase Agreement dated as of December 16, 2014 (as amended, the “Receivables Purchase Agreement”) by and between First Canada and CIBC Mellon Trust Company, in its capacity as trustee of P…

Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant. The information provided in

Entry into a Material Definitive Agreement. On December 4, 2025, Wintrust Financial Corporation ("Wintrust") entered into the Fourth Amendment to Amended and Restated Credit Agreement dated December 4, 2025 (the "Fourth Amendment"), among Wintrust, the lenders named therein, and U.S. Bank National Association, as administrative agent. Capitalized terms used but not defined herein shall have the respective meanings ascribed to them by the Amended and Restated Credit Agreement dated December 12…

Results of Operations and Financial Condition The information in this Current Report is being furnished and shall not be deemed “filed” for the purposes of Section 18 of the Securities Exchange Act of 1934, as amended, or otherwise subject to the liabilities of that Section. The information in this Current Report shall not be incorporated by reference into any registration statement or other document pursuant to the Securities Act of 1933, as amended. On October 20, 2025, Wintrust Financial C…

Director — Laura Kohl, David S. Richter: Two new directors were appointed to the Board of Directors.

Results of Operations and Financial Condition The information in this Current Report is being furnished and shall not be deemed “filed” for the purposes of Section 18 of the Securities Exchange Act of 1934, as amended, or otherwise subject to the liabilities of that Section. The information in this Current Report shall not be incorporated by reference into any registration statement or other document pursuant to the Securities Act of 1933, as amended. On July 21, 2025, Wintrust Financial Corp…

Material Modification to Rights of Security Holders. On July 15, 2025, Wintrust Financial Corporation (the “Company”) filed with the Secretary of the State of Illinois two Statements of Resolution (the “Modifications”) relating to the Company’s Amended and Restated Articles of Incorporation, as amended. The Modifications were filed solely to formally reflect that no shares of the Company’s Fixed-to-Floating Rate Non-Cumulative Perpetual Preferred Stock, Series D, no par value per share (the “…

Director — Richard L. Postma: A director resigned for personal reasons without any reported disagreement with the company, representing a standard board departure.

The filing discloses the approval of a stock incentive plan, which is a compensatory arrangement rather than a change in management personnel.

Other Events. On May 22, 2025, Wintrust Financial Corporation (the “Company”) completed its previously disclosed public offering of 17,000,000 depositary shares (the “Depositary Shares”), each representing a 1/1,000th interest in a share of the Company’s 7.875% Fixed-Rate Reset Non-Cumulative Perpetual Preferred Stock, Series F, no par value per share (the “Series F Preferred Stock”), with a liquidation preference of $25,000 per share (equivalent to $25.00 per Depositary Share). The Depositar…

of the Company’s Current Report on Form 8-K filed on May 14, 2025 for a description of certain terms of the Series F Preferred Stock. Such description is qualified in its entirety by reference to the Company’s Certificate of Designations relating to the Series F Preferred Stock, as filed with the Secretary of State of the State of Illinois on May 9, 2025, which is incorporated by reference herein as Exhibit 4.1 hereto. In connection with the issuance of the Depositary Shares, on May 22, 2025,…

Material Modification to the Rights of Security Holders . In connection with the previously disclosed underwritten public offering by Wintrust Financial Corporation (the “Company”) of 17,000,000 depositary shares, each representing a 1/1,000th interest in a share of the Company’s Series F Preferred Stock (as defined below), the Company is establishing a new series of preferred stock, designated as the “7.875% Fixed-Rate Reset Non-Cumulative Perpetual Preferred Stock, Series F,” no par value p…

Entry into a Material Definitive Agreement . On May 8, 2025, Wintrust Financial Corporation (the “Company”) entered into an Underwriting Agreement (the “Underwriting Agreement”) with RBC Capital Markets, LLC, as representative of the several underwriters named in Schedule A thereto (the “Underwriters”), providing for the offer and sale in a firm commitment underwritten public offering (the “Offering”) of 17,000,000 depositary shares (the “Depositary Shares”), each representing a 1/1,000th int…

Results of Operations and Financial Condition The information in this Current Report is being furnished and shall not be deemed “filed” for the purposes of Section 18 of the Securities Exchange Act of 1934, as amended, or otherwise subject to the liabilities of that Section. The information in this Current Report shall not be incorporated by reference into any registration statement or other document pursuant to the Securities Act of 1933, as amended. On April 21, 2025, Wintrust Financial Cor…

Results of Operations and Financial Condition The information in this Current Report is being furnished and shall not be deemed “filed” for the purposes of Section 18 of the Securities Exchange Act of 1934, as amended, or otherwise subject to the liabilities of that Section. The information in this Current Report shall not be incorporated by reference into any registration statement or other document pursuant to the Securities Act of 1933, as amended. On January 21, 2025, Wintrust Financial C…

Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant. The information provided in

Entry into a Material Definitive Agreement. On December 6, 2024, Wintrust Financial Corporation ("Wintrust") entered into the Third Amendment to Amended and Restated Credit Agreement and First Amendment to Amended and Restated Pledge and Security Agreement, dated December 6, 2024, among Wintrust, the lenders named therein, and U.S. Bank, National Association, as administrative agent ("Amendment"). Capitalized terms used but not defined herein shall have the respective meanings ascribed to the…

Results of Operations and Financial Condition The information in this Current Report is being furnished and shall not be deemed “filed” for the purposes of Section 18 of the Securities Exchange Act of 1934, as amended, or otherwise subject to the liabilities of that Section. The information in this Current Report shall not be incorporated by reference into any registration statement or other document pursuant to the Securities Act of 1933, as amended. On October 21, 2024, Wintrust Financial C…

Entry into a Material Definitive Agreement. On August 29, 2024, an indirect subsidiary of Wintrust Financial Corporation (“Wintrust”), First Insurance Funding of Canada Inc. (“First Canada) entered into the Twelfth Amending Agreement, dated as of August 29, 2024 (the “Amendment”) to the Receivables Purchase Agreement dated as of December 16, 2014 (as amended, the “Receivables Purchase Agreement”) by and between First Canada and CIBC Mellon Trust Company, in its capacity as trustee of Plaza Tr…

Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant. The information provided in

Other Events On August 1, 2024, Wintrust and Macatawa issued a joint press release announcing the completion of the previously announced acquisition of Macatawa in accordance with the Agreement and Plan of Merger, dated as of April 15, 2024 (the “Merger Agreement”), by and among Macatawa, Wintrust and Leo Subsidiary LLC, a wholly owned subsidiary of Wintrust (“Merger Sub”). Under the Merger Agreement, Macatawa merged with and into Merger Sub, with Merger Sub surviving as a wholly-owned subsid…