Results of Operations and Financial Condition On July 24, 2026, Tompkins Financial Corporation, (the “Company”) issued a press release announcing its earnings for the calendar quarter ended June 30, 2026. A copy of the press release is attached to this Report on Form 8-K as Exhibit 99.1 and is incorporated herein by reference. The information furnished under Items 2.02 and

Other Events On July 23, 2026 , the Company's Board of Directors declared a dividend of $0.70 per share, payable on August 14, 2026, to common shareholders of record on August 7, 2026. A copy of the press release is attached to this Report on Form 8-K as Exhibit 99.2.

President of Tompkins Community Bank and Executive Vice President of Tompkins Financial Corporation — Phillip M. Quintana: Phillip M. Quintana has been promoted to President of Tompkins Community Bank and Executive Vice President of Tompkins Financial Corporation.

Other Events On April 23, 2026 , the Company's Board of Directors declared a dividend of $0.67 per share, payable on May 15, 2026, to common shareholders of record on May 8, 2026. A copy of the press release is attached to this Report on Form 8-K as Exhibit 99.2.

Results of Operations and Financial Condition On April 24, 2026, Tompkins Financial Corporation, (the “Company”) issued a press release announcing its earnings for the calendar quarter ended March 31, 2026. A copy of the press release is attached to this Report on Form 8-K as Exhibit 99.1 and is incorporated herein by reference. The information furnished under Items 2.02 and

Other Events On January 29, 2026 , the Company's Board of Directors declared a dividend of $0.67 per share, payable on February 22, 2026, to common shareholders of record on February 13, 2026. A copy of the press release is attached to this Report on Form 8-K as Exhibit 99.2.

Results of Operations and Financial Condition On January 30, 2026, Tompkins Financial Corporation, (the “Company”) issued a press release announcing its earnings for the calendar quarter ended December 31, 2025. A copy of the press release is attached to this Report on Form 8-K as Exhibit 99.1 and is incorporated herein by reference. The information furnished under Items 2.02 and

CFO — Matthew D. Tomazin: The filing discloses the establishment of supplemental executive retirement plans (compensatory arrangements) for the CFO and CEO, not a departure or change in management status.

Other Events On November 3, 2025, the Company sold $565.0 million of available-for-sale debt securities with an average book yield of 1.56%, resulting in an pre-tax loss of approximately $79.5 million, and reinvested in $565.0 million of debt securities with an estimated average book yield of 4.52%. "Safe Harbor" Statement under the Private Securities Litigation Reform Act of 1995: This report contains "forward-looking statements" within the meaning of the Private Securities Litigation Reform…

Entry into Material Definitive Agreement. On October 31, 2025, Tompkins Financial Corporation (the “Company”), Tompkins Insurance Agencies, Inc. (“TIA”), a wholly-owned subsidiary of the Company, and Arthur J. Gallagher Risk Management Services, LLC, an affiliate of Arthur J. Gallagher & Co. (collectively, “Gallagher”) entered into a definitive stock purchase agreement (the “Purchase Agreement”), pursuant to which the Company sold all of the issued and outstanding shares of capital stock of T…

CEO — David S. Boyce: The CEO of a subsidiary ceased employment in connection with a corporate transaction, constituting a genuine executive departure, though the context suggests an orderly exit rather than a sudden shock.

Completion of Acquisition or Disposition of Assets. The information set forth in

Other Events On October 23, 2025 , the Company's Board of Directors declared a dividend of $0.65 per share, payable on November 14, 2025, to common shareholders of record on November 7, 2025. A copy of the press release is attached to this Report on Form 8-K as Exhibit 99.2.

Results of Operations and Financial Condition On October 24, 2025, Tompkins Financial Corporation, (the “Company”) issued a press release announcing its earnings for the calendar quarter ended September 30, 2025. A copy of the press release is attached to this Report on Form 8-K as Exhibit 99.1 and is incorporated herein by reference. The information furnished under Items 2.02 and

Results of Operations and Financial Condition On July 25, 2025, Tompkins Financial Corporation, (the “Company”) issued a press release announcing its earnings for the calendar quarter ended June 30, 2025. A copy of the press release is attached to this Report on Form 8-K as Exhibit 99.1 and is incorporated herein by reference. The information furnished under Items 2.02 and

Other Events On July 24, 2025 , the Company's Board of Directors declared a dividend of $0.62 per share, payable on August 15, 2025, to common shareholders of record on August 8, 2025. A copy of the press release is attached to this Report on Form 8-K as Exhibit 99.2. On July 25, 2025, the Company announced that its Board of Directors has approved a new stock repurchase program, authorizing the Company to repurchase up to 400,000 shares of the Company’s outstanding common stock, par value $0.…

Other Events On April 24, 2025 , the Company's Board of Directors declared a dividend of $0.62 per share, payable on May 16, 2025, to common shareholders of record on May 9, 2025. A copy of the press release is attached to this Report on Form 8-K as Exhibit 99.2.

Executive Vice President — John McKenna: The filing announces a planned retirement of a senior executive (EVP/President of the Bank) in the future (summer 2026), which constitutes an orderly succession rather than a sudden loss or shock.

Results of Operations and Financial Condition On April 25, 2025, Tompkins Financial Corporation, (the “Company”) issued a press release announcing its earnings for the calendar quarter ended March 31, 2025. A copy of the press release is attached to this Report on Form 8-K as Exhibit 99.1 and is incorporated herein by reference. The information furnished under Items 2.02 and

Other Events On January 30, 2024, the Company's Board of Directors declared a dividend of $0.62 per share, payable on February 21, 2025, to common shareholders of record on February 14, 2025. A copy of the press release is attached to this Report on Form 8-K as Exhibit 99.2.

Results of Operations and Financial Condition On January 31, 2025, Tompkins Financial Corporation, (the “Company”) issued a press release announcing its earnings for the calendar quarter ended December 31, 2024. A copy of the press release is attached to this Report on Form 8-K as Exhibit 99.1 and is incorporated herein by reference. The information furnished under Items 2.02 and

Results of Operations and Financial Condition On October 25, 2024, Tompkins Financial Corporation, (the “Company”) issued a press release announcing its earnings for the calendar quarter ended September 30, 2024. A copy of the press release is attached to this Report on Form 8-K as Exhibit 99.1 and is incorporated herein by reference. The information furnished under Items 2.02 and

Other Events On October 24, 2024, the Company's Board of Directors declared a dividend of $0.62 per share, payable on November 15, 2024, to common shareholders of record on November 8, 2024. A copy of the press release, is attached to this Report on Form 8-K as Exhibit 99.2.

Chair — Thomas R. Rochon: The Chair is retiring due to mandatory age limits with a pre-identified internal successor, representing an orderly succession rather than a sudden loss.

Other Events On April 25, 2024, the Company's Board of Directors declared a dividend of $0.61 per share, payable on August 16, 2024, to common shareholders of record on August 9, 2024. A copy of the press release, is attached to this Report on Form 8-K as Exhibit 99.2.