TMP

SEC source: 0001127602-21-010179 · form4.xml · derivative · entry 5

KLEIN GERALD J JR · CIK 0001384977 · EVP Pres&CEO Mahopac Bank

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 3,055 shares

Expires 2023-05-03

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · derivative.exercise_date: Stock Appreciation Rights (SARs) were granted pursuant to the Tompkins Financial Corporation 2009 Equity Plan. SARs have a seven year vesting schedule with 0% vesting in year one, 17% vesting in years two through six, and 15% vesting in year seven. When exercised, the SARs will be settled in Common Stock of the Company. The grant will expire ten years from the date of the grant.

SEC source: 0001127602-21-010179 · form4.xml · nonDerivative · entry 2

KLEIN GERALD J JR · CIK 0001384977 · EVP Pres&CEO Mahopac Bank

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 29,027

F1 · shares: Shares withheld for option cost and taxes.

SEC source: 0001127602-21-010179 · form4.xml · nonDerivative · entry 1

KLEIN GERALD J JR · CIK 0001384977 · EVP Pres&CEO Mahopac Bank

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 31,123

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

SEC source: 0001127602-21-008588 · form4.xml · derivative · entry 11

BOYCE DAVID S · CIK 0001201524 · EVP, Pres. & CEO Tompkins Ins.

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 716

Underlying: Common Stock · 380 shares

Expires 2025-11-04

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · derivative.exercise_date: Stock Appreciation Rights (SARs) were granted pursuant to the Tompkins Financial Corporation 2009 Equity Plan. SARs have a seven year vesting schedule with 0% vesting in year one, 17% vesting in years two through six, and 15% vesting in year seven. When exercised, the SARs will be settled in Common Stock of the Company. The grant will expire ten years from the date of the grant.

SEC source: 0001127602-21-008588 · form4.xml · derivative · entry 10

BOYCE DAVID S · CIK 0001201524 · EVP, Pres. & CEO Tompkins Ins.

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 522

Underlying: Common Stock · 590 shares

Expires 2024-11-21

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · derivative.exercise_date: Stock Appreciation Rights (SARs) were granted pursuant to the Tompkins Financial Corporation 2009 Equity Plan. SARs have a seven year vesting schedule with 0% vesting in year one, 17% vesting in years two through six, and 15% vesting in year seven. When exercised, the SARs will be settled in Common Stock of the Company. The grant will expire ten years from the date of the grant.

SEC source: 0001127602-21-008588 · form4.xml · derivative · entry 9

BOYCE DAVID S · CIK 0001201524 · EVP, Pres. & CEO Tompkins Ins.

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 459 shares

Expires 2023-05-03

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · derivative.exercise_date: Stock Appreciation Rights (SARs) were granted pursuant to the Tompkins Financial Corporation 2009 Equity Plan. SARs have a seven year vesting schedule with 0% vesting in year one, 17% vesting in years two through six, and 15% vesting in year seven. When exercised, the SARs will be settled in Common Stock of the Company. The grant will expire ten years from the date of the grant.

SEC source: 0001127602-21-008588 · form4.xml · nonDerivative · entry 6

BOYCE DAVID S · CIK 0001201524 · EVP, Pres. & CEO Tompkins Ins.

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 25,247

F1 · shares: Shares withheld for option cost and taxes.

SEC source: 0001127602-21-008588 · form4.xml · nonDerivative · entry 5

BOYCE DAVID S · CIK 0001201524 · EVP, Pres. & CEO Tompkins Ins.

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 25,558

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

SEC source: 0001127602-21-008588 · form4.xml · nonDerivative · entry 4

BOYCE DAVID S · CIK 0001201524 · EVP, Pres. & CEO Tompkins Ins.

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 25,178

F1 · shares: Shares withheld for option cost and taxes.

SEC source: 0001127602-21-008588 · form4.xml · nonDerivative · entry 3

BOYCE DAVID S · CIK 0001201524 · EVP, Pres. & CEO Tompkins Ins.

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 25,625

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

SEC source: 0001127602-21-008588 · form4.xml · nonDerivative · entry 2

BOYCE DAVID S · CIK 0001201524 · EVP, Pres. & CEO Tompkins Ins.

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 25,035

F1 · shares: Shares withheld for option cost and taxes.

SEC source: 0001127602-21-008588 · form4.xml · nonDerivative · entry 1

BOYCE DAVID S · CIK 0001201524 · EVP, Pres. & CEO Tompkins Ins.

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 25,349

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

SEC source: 0001127602-21-005569 · form4.xml · nonDerivative · entry 1

Rahilly Ita M · CIK 0001811767 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,116.91

F1 · shares: Automatic monthly purchase through Tompkins Financial Dividend Reinvestment and Stock Purchase and Sale Plan.

SEC source: 0001127602-21-024500 · form4.xml · nonDerivative · entry 1

HARTZ GREGORY J · CIK 0001384976 · EVP, Pres.&CEO Tompkins Trust

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 24,773.704

F1 · shares: Bona fide gift to Charitable Gift Account

SEC source: 0001127602-21-004615 · form4.xml · nonDerivative · entry 1

FETSKO FRANCIS M · CIK 0001131014 · EVP, COO, CFO & Treasurer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 23,051

F1 · shares: Deemed disposition of shares to the issuer to pay for taxes upon vesting of restricted stock.

SEC source: 0001127602-21-004254 · form4.xml · derivative · entry 2

YUNKER CRAIG · CIK 0001104704 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,939.032

Underlying: Common Stock · 1,939.032 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · derivative.exercise_price: Each share of phantom stock is the economic equivalent of one share of common stock. Phantom stock represents deferred stock compensation under the Amended and Restated Retainer Plan for Eligible Directors of Tompkins Financial Corporation and its Wholly-Owned Subsidiaries. These shares are held in a rabbi trust pending distribution upon the occurrence of certain events specified in the Plan. The reporting person has no voting or investment power over the shares prior to such distribution.

F1 · shares: Includes change in beneficial ownership of 1,939.032 shares from Indirect to Direct as a result of a distribution pursuant to the Directors' Deferred Stock Retainer Agreement.

F2 · derivative.exercise_date: Each share of phantom stock is the economic equivalent of one share of common stock. Phantom stock represents deferred stock compensation under the Amended and Restated Retainer Plan for Eligible Directors of Tompkins Financial Corporation and its Wholly-Owned Subsidiaries. These shares are held in a rabbi trust pending distribution upon the occurrence of certain events specified in the Plan. The reporting person has no voting or investment power over the shares prior to such distribution.

F2 · derivative.expiration_date: Each share of phantom stock is the economic equivalent of one share of common stock. Phantom stock represents deferred stock compensation under the Amended and Restated Retainer Plan for Eligible Directors of Tompkins Financial Corporation and its Wholly-Owned Subsidiaries. These shares are held in a rabbi trust pending distribution upon the occurrence of certain events specified in the Plan. The reporting person has no voting or investment power over the shares prior to such distribution.

SEC source: 0001127602-21-004254 · form4.xml · nonDerivative · entry 1

YUNKER CRAIG · CIK 0001104704 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 27,921.931

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · shares: Includes change in beneficial ownership of 1,939.032 shares from Indirect to Direct as a result of a distribution pursuant to the Directors' Deferred Stock Retainer Agreement.

SEC source: 0001127602-21-004252 · form4.xml · derivative · entry 2

Johnson Patricia A · CIK 0001362027 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,469.94

Underlying: Common Stock · 617.485 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · derivative.exercise_price: Each share of phantom stock is the economic equivalent of one share of common stock. Phantom stock represents deferred stock compensation under the Amended and Restated Retainer Plan for Eligible Directors of Tompkins Financial Corporation and its Wholly-Owned Subsidiaries. These shares are held in a rabbi trust pending distribution upon the occurrence of certain events specified in the Plan. The reporting person has no voting or investment power over the shares prior to such distribution.

F1 · shares: Includes change in beneficial ownership of 617.485 shares from Indirect to Direct as a result of a distribution pursuant to the Directors' Deferred Stock Retainer Agreement.

F2 · derivative.exercise_date: Each share of phantom stock is the economic equivalent of one share of common stock. Phantom stock represents deferred stock compensation under the Amended and Restated Retainer Plan for Eligible Directors of Tompkins Financial Corporation and its Wholly-Owned Subsidiaries. These shares are held in a rabbi trust pending distribution upon the occurrence of certain events specified in the Plan. The reporting person has no voting or investment power over the shares prior to such distribution.

F2 · derivative.expiration_date: Each share of phantom stock is the economic equivalent of one share of common stock. Phantom stock represents deferred stock compensation under the Amended and Restated Retainer Plan for Eligible Directors of Tompkins Financial Corporation and its Wholly-Owned Subsidiaries. These shares are held in a rabbi trust pending distribution upon the occurrence of certain events specified in the Plan. The reporting person has no voting or investment power over the shares prior to such distribution.

SEC source: 0001127602-21-004252 · form4.xml · nonDerivative · entry 1

Johnson Patricia A · CIK 0001362027 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 757.3

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · shares: Includes change in beneficial ownership of 617.485 shares from Indirect to Direct as a result of a distribution pursuant to the Directors' Deferred Stock Retainer Agreement.

SEC source: 0001127602-21-004250 · form4.xml · derivative · entry 3

BATTAGLIA PAUL J. · CIK 0001491721 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 9,989.936

Underlying: Common Stock · 1,664.989 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · derivative.exercise_price: Each share of phantom stock is the economic equivalent of one share of common stock. Phantom stock represents deferred stock compensation under the Amended and Restated Retainer Plan for Eligible Directors of Tompkins Financial Corporation and its Wholly-Owned Subsidiaries. These shares are held in a rabbi trust pending distribution upon the occurrence of certain events specified in the Plan. The reporting person has no voting or investment power over the shares prior to such distribution.

F1 · shares: Includes change in beneficial ownership of 1664.989 shares from Indirect to Direct as a result of distribution pursuant to the Directors' Deferred Stock Retainer Agreement.

F2 · derivative.exercise_date: Each share of phantom stock is the economic equivalent of one share of common stock. Phantom stock represents deferred stock compensation under the Amended and Restated Retainer Plan for Eligible Directors of Tompkins Financial Corporation and its Wholly-Owned Subsidiaries. These shares are held in a rabbi trust pending distribution upon the occurrence of certain events specified in the Plan. The reporting person has no voting or investment power over the shares prior to such distribution.

F2 · derivative.expiration_date: Each share of phantom stock is the economic equivalent of one share of common stock. Phantom stock represents deferred stock compensation under the Amended and Restated Retainer Plan for Eligible Directors of Tompkins Financial Corporation and its Wholly-Owned Subsidiaries. These shares are held in a rabbi trust pending distribution upon the occurrence of certain events specified in the Plan. The reporting person has no voting or investment power over the shares prior to such distribution.

SEC source: 0001127602-21-004250 · form4.xml · nonDerivative · entry 1

BATTAGLIA PAUL J. · CIK 0001491721 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,664.989

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · shares: Includes change in beneficial ownership of 1664.989 shares from Indirect to Direct as a result of distribution pursuant to the Directors' Deferred Stock Retainer Agreement.

SEC source: 0001127602-21-001564 · form4.xml · nonDerivative · entry 1

Rahilly Ita M · CIK 0001811767 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,083.968

F1 · price: Automatic monthly purchase through Tompkins Financial Dividend Reinvestment and Stock Purchase and Sale Plan.

SEC source: 0001127602-21-001502 · form4.xml · nonDerivative · entry 1

Rochon Thomas R. · CIK 0001463129 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 436.1467

F1 · price: Represents shares of common stock elected to be received by the reporting person in lieu of cash retainer fees pursuant to the Second Amended and Restated Retainer Plan for Eligible Directors of Tompkins Financial Corporation and its Wholly-Owned Subsidiaries.

SEC source: 0001127602-21-001406 · form4.xml · derivative · entry 1

Rochon Thomas R. · CIK 0001463129 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 15,551.165

Underlying: Common Stock · 129.481 shares

Expires not disclosed

F1 · derivative.exercise_price: Each share of phantom stock is the economic equivalent of one share of common stock. Phantom stock represents deferred stock compensation under the Amended and Restated Retainer Plan for Eligible Directors of Tompkins Financial Corporation and its Wholly-Owned Subsidiaries. These shares are held in a rabbi trust pending distribution upon the occurrence of certain events specified in the Plan. The reporting person has no voting or investment power over the shares prior to such distribution.

F1 · derivative.exercise_date: Each share of phantom stock is the economic equivalent of one share of common stock. Phantom stock represents deferred stock compensation under the Amended and Restated Retainer Plan for Eligible Directors of Tompkins Financial Corporation and its Wholly-Owned Subsidiaries. These shares are held in a rabbi trust pending distribution upon the occurrence of certain events specified in the Plan. The reporting person has no voting or investment power over the shares prior to such distribution.

F1 · derivative.expiration_date: Each share of phantom stock is the economic equivalent of one share of common stock. Phantom stock represents deferred stock compensation under the Amended and Restated Retainer Plan for Eligible Directors of Tompkins Financial Corporation and its Wholly-Owned Subsidiaries. These shares are held in a rabbi trust pending distribution upon the occurrence of certain events specified in the Plan. The reporting person has no voting or investment power over the shares prior to such distribution.

SEC source: 0001127602-21-001405 · form4.xml · derivative · entry 1

WEBER ALFRED J · CIK 0001225242 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 4,281.106

Underlying: Common Stock · 110.661 shares

Expires not disclosed

F1 · derivative.exercise_price: Each share of phantom stock is the economic equivalent of one share of common stock. Phantom stock represents deferred stock compensation under the Amended and Restated Retainer Plan for Eligible Directors of Tompkins Financial Corporation and its Wholly-Owned Subsidiaries. These shares are held in a rabbi trust pending distribution upon the occurrence of certain events specified in the Plan. The reporting person has no voting or investment power over the shares prior to such distribution.

F1 · derivative.exercise_date: Each share of phantom stock is the economic equivalent of one share of common stock. Phantom stock represents deferred stock compensation under the Amended and Restated Retainer Plan for Eligible Directors of Tompkins Financial Corporation and its Wholly-Owned Subsidiaries. These shares are held in a rabbi trust pending distribution upon the occurrence of certain events specified in the Plan. The reporting person has no voting or investment power over the shares prior to such distribution.

F1 · derivative.expiration_date: Each share of phantom stock is the economic equivalent of one share of common stock. Phantom stock represents deferred stock compensation under the Amended and Restated Retainer Plan for Eligible Directors of Tompkins Financial Corporation and its Wholly-Owned Subsidiaries. These shares are held in a rabbi trust pending distribution upon the occurrence of certain events specified in the Plan. The reporting person has no voting or investment power over the shares prior to such distribution.

SEC source: 0001127602-21-001404 · form4.xml · derivative · entry 2

Tegan Jennifer R · CIK 0001781908 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,390.477

Underlying: Common Stock · 120.985 shares

Expires not disclosed

F1 · derivative.exercise_price: Each share of phantom stock is the economic equivalent of one share of common stock. Phantom stock represents deferred stock compensation under the Amended and Restated Retainer Plan for Eligible Directors of Tompkins Financial Corporation and its Wholly-Owned Subsidiaries. These shares are held in a rabbi trust pending distribution upon the occurrence of certain events specified in the Plan. The reporting person has no voting or investment power over the shares prior to such distribution.

F1 · derivative.exercise_date: Each share of phantom stock is the economic equivalent of one share of common stock. Phantom stock represents deferred stock compensation under the Amended and Restated Retainer Plan for Eligible Directors of Tompkins Financial Corporation and its Wholly-Owned Subsidiaries. These shares are held in a rabbi trust pending distribution upon the occurrence of certain events specified in the Plan. The reporting person has no voting or investment power over the shares prior to such distribution.

F1 · derivative.expiration_date: Each share of phantom stock is the economic equivalent of one share of common stock. Phantom stock represents deferred stock compensation under the Amended and Restated Retainer Plan for Eligible Directors of Tompkins Financial Corporation and its Wholly-Owned Subsidiaries. These shares are held in a rabbi trust pending distribution upon the occurrence of certain events specified in the Plan. The reporting person has no voting or investment power over the shares prior to such distribution.

SEC source: 0001127602-21-001404 · form4.xml · derivative · entry 1

Tegan Jennifer R · CIK 0001781908 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,269.492

Underlying: Common Stock · 79.366 shares

Expires not disclosed

F1 · derivative.exercise_price: Each share of phantom stock is the economic equivalent of one share of common stock. Phantom stock represents deferred stock compensation under the Amended and Restated Retainer Plan for Eligible Directors of Tompkins Financial Corporation and its Wholly-Owned Subsidiaries. These shares are held in a rabbi trust pending distribution upon the occurrence of certain events specified in the Plan. The reporting person has no voting or investment power over the shares prior to such distribution.

F1 · derivative.exercise_date: Each share of phantom stock is the economic equivalent of one share of common stock. Phantom stock represents deferred stock compensation under the Amended and Restated Retainer Plan for Eligible Directors of Tompkins Financial Corporation and its Wholly-Owned Subsidiaries. These shares are held in a rabbi trust pending distribution upon the occurrence of certain events specified in the Plan. The reporting person has no voting or investment power over the shares prior to such distribution.

F1 · derivative.expiration_date: Each share of phantom stock is the economic equivalent of one share of common stock. Phantom stock represents deferred stock compensation under the Amended and Restated Retainer Plan for Eligible Directors of Tompkins Financial Corporation and its Wholly-Owned Subsidiaries. These shares are held in a rabbi trust pending distribution upon the occurrence of certain events specified in the Plan. The reporting person has no voting or investment power over the shares prior to such distribution.

SEC source: 0001127602-21-001403 · form4.xml · derivative · entry 1

SPAIN MICHAEL H · CIK 0001124188 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 8,320.507

Underlying: Common Stock · 96.788 shares

Expires not disclosed

F1 · derivative.exercise_price: Each share of phantom stock is the economic equivalent of one share of common stock. Phantom stock represents deferred stock compensation under the Amended and Restated Retainer Plan for Eligible Directors of Tompkins Financial Corporation and its Wholly-Owned Subsidiaries. These shares are held in a rabbi trust pending distribution upon the occurrence of certain events specified in the Plan. The reporting person has no voting or investment power over the shares prior to such distribution.

F1 · derivative.exercise_date: Each share of phantom stock is the economic equivalent of one share of common stock. Phantom stock represents deferred stock compensation under the Amended and Restated Retainer Plan for Eligible Directors of Tompkins Financial Corporation and its Wholly-Owned Subsidiaries. These shares are held in a rabbi trust pending distribution upon the occurrence of certain events specified in the Plan. The reporting person has no voting or investment power over the shares prior to such distribution.

F1 · derivative.expiration_date: Each share of phantom stock is the economic equivalent of one share of common stock. Phantom stock represents deferred stock compensation under the Amended and Restated Retainer Plan for Eligible Directors of Tompkins Financial Corporation and its Wholly-Owned Subsidiaries. These shares are held in a rabbi trust pending distribution upon the occurrence of certain events specified in the Plan. The reporting person has no voting or investment power over the shares prior to such distribution.

SEC source: 0001127602-21-001402 · form4.xml · derivative · entry 1

Fessenden Daniel J. · CIK 0001463126 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 4,582.464

Underlying: Common Stock · 148.409 shares

Expires not disclosed

F1 · derivative.exercise_price: Each share of phantom stock is the economic equivalent of one share of common stock. Phantom stock represents deferred stock compensation under the Amended and Restated Retainer Plan for Eligible Directors of Tompkins Financial Corporation and its Wholly-Owned Subsidiaries. These shares are held in a rabbi trust pending distribution upon the occurrence of certain events specified in the Plan. The reporting person has no voting or investment power over the shares prior to such distribution.

F1 · derivative.exercise_date: Each share of phantom stock is the economic equivalent of one share of common stock. Phantom stock represents deferred stock compensation under the Amended and Restated Retainer Plan for Eligible Directors of Tompkins Financial Corporation and its Wholly-Owned Subsidiaries. These shares are held in a rabbi trust pending distribution upon the occurrence of certain events specified in the Plan. The reporting person has no voting or investment power over the shares prior to such distribution.

F1 · derivative.expiration_date: Each share of phantom stock is the economic equivalent of one share of common stock. Phantom stock represents deferred stock compensation under the Amended and Restated Retainer Plan for Eligible Directors of Tompkins Financial Corporation and its Wholly-Owned Subsidiaries. These shares are held in a rabbi trust pending distribution upon the occurrence of certain events specified in the Plan. The reporting person has no voting or investment power over the shares prior to such distribution.

SEC source: 0001127602-21-001401 · form4.xml · derivative · entry 2

ALEXANDER JOHN E · CIK 0001074514 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 18,662.045

Underlying: Common Stock · 126.147 shares

Expires not disclosed

F1 · derivative.exercise_price: Each share of phantom stock is the economic equivalent of one share of common stock. Phantom stock represents deferred stock compensation under the Amended and Restated Retainer Plan for Eligible Directors of Tompkins Financial Corporation and its Wholly-Owned Subsidiaries. These shares are held in a rabbi trust pending distribution upon the occurrence of certain events specified in the Plan. The reporting person has no voting or investment power over the shares prior to such distribution.

F1 · derivative.exercise_date: Each share of phantom stock is the economic equivalent of one share of common stock. Phantom stock represents deferred stock compensation under the Amended and Restated Retainer Plan for Eligible Directors of Tompkins Financial Corporation and its Wholly-Owned Subsidiaries. These shares are held in a rabbi trust pending distribution upon the occurrence of certain events specified in the Plan. The reporting person has no voting or investment power over the shares prior to such distribution.

F1 · derivative.expiration_date: Each share of phantom stock is the economic equivalent of one share of common stock. Phantom stock represents deferred stock compensation under the Amended and Restated Retainer Plan for Eligible Directors of Tompkins Financial Corporation and its Wholly-Owned Subsidiaries. These shares are held in a rabbi trust pending distribution upon the occurrence of certain events specified in the Plan. The reporting person has no voting or investment power over the shares prior to such distribution.

SEC source: 0001127602-21-001401 · form4.xml · derivative · entry 1

ALEXANDER JOHN E · CIK 0001074514 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 18,535.898

Underlying: Common Stock · 61.945 shares

Expires not disclosed

F1 · derivative.exercise_price: Each share of phantom stock is the economic equivalent of one share of common stock. Phantom stock represents deferred stock compensation under the Amended and Restated Retainer Plan for Eligible Directors of Tompkins Financial Corporation and its Wholly-Owned Subsidiaries. These shares are held in a rabbi trust pending distribution upon the occurrence of certain events specified in the Plan. The reporting person has no voting or investment power over the shares prior to such distribution.

F1 · derivative.exercise_date: Each share of phantom stock is the economic equivalent of one share of common stock. Phantom stock represents deferred stock compensation under the Amended and Restated Retainer Plan for Eligible Directors of Tompkins Financial Corporation and its Wholly-Owned Subsidiaries. These shares are held in a rabbi trust pending distribution upon the occurrence of certain events specified in the Plan. The reporting person has no voting or investment power over the shares prior to such distribution.

F1 · derivative.expiration_date: Each share of phantom stock is the economic equivalent of one share of common stock. Phantom stock represents deferred stock compensation under the Amended and Restated Retainer Plan for Eligible Directors of Tompkins Financial Corporation and its Wholly-Owned Subsidiaries. These shares are held in a rabbi trust pending distribution upon the occurrence of certain events specified in the Plan. The reporting person has no voting or investment power over the shares prior to such distribution.

SEC source: 0001127602-20-031310 · form4.xml · nonDerivative · entry 1

Rahily Ita M · CIK 0001811767 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,051.021

F1 · shares: Automatic monthly purchase through Tompkins Financial Dividend Reinvestment and Stock Purchase and Sale Plan.

SEC source: 0001127602-20-030257 · form4.xml · nonDerivative · entry 1

HARTZ GREGORY J · CIK 0001384976 · EVP, Pres.&CEO Tompkins Trust

10b5-1 filing: Not disclosed

Ownership: Indirect · As Custodian FBO Andrew Chase UGMA/NY

Disclosed balance after: 18.887

F1 · shares: Purchase of shares as gift for grandchild for whom reporting person is Custodian.

SEC source: 0001127602-20-029824 · form4.xml · nonDerivative · entry 1

McKenna John M · CIK 0001615770 · EVP, Tompkins Bank of Castile

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 11,834.915

F1 · shares: Deemed disposition of shares to Issuer to satisfy option cost and taxes.

SEC source: 0001127602-20-029818 · form4.xml · nonDerivative · entry 1

KLEIN GERALD J JR · CIK 0001384977 · EVP Pres&CEO Mahopac Bank

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 28,068

F1 · shares: Deemed disposition of shares to the issuer to pay for taxes upon vesting of restricted stock.

SEC source: 0001127602-20-029814 · form4.xml · nonDerivative · entry 1

GRUBER SCOTT L · CIK 0001481104 · EVP, Pres. & CEO, VIST Bank

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 13,469.182

F1 · shares: Deemed disposition of shares to the Issuer to pay for taxes upon vesting of restricted stock.

SEC source: 0001127602-20-029898 · form4.xml · nonDerivative · entry 1

VALENTI SUSAN M. · CIK 0001548384 · EVP, Corporate Marketing

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 14,217.398

SEC source: 0001127602-20-029897 · form4.xml · nonDerivative · entry 1

ROMAINE STEPHEN S · CIK 0001201525 · Director · President & CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 57,173.697

F1 · shares: Deemed disposition of shares to the Issuer to pay for taxes upon vesting of restricted stock.

SEC source: 0001127602-20-029896 · form4.xml · nonDerivative · entry 1

BOYCE DAVID S · CIK 0001201524 · EVP, Pres. & CEO Tompkins Ins.

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 24,890

F1 · shares: Deemed disposition of shares to the Issuer to pay for taxes upon vesting of restricted stock.

SEC source: 0001127602-20-029895 · form4.xml · nonDerivative · entry 1

FETSKO FRANCIS M · CIK 0001131014 · EVP, COO, CFO & Treasurer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 23,070

F1 · shares: Deemed disposition of shares to the issuer to pay for taxes upon vesting of restricted stock.

SEC source: 0001127602-20-029893 · form4.xml · nonDerivative · entry 1

HARTZ GREGORY J · CIK 0001384976 · EVP, Pres.&CEO Tompkins Trust

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 24,848.704

F1 · shares: Deemed disposition of shares to the Issuer to pay for taxes upon vesting of restricted stock.

SEC source: 0001127602-20-029817 · form4.xml · nonDerivative · entry 1

Rahily Ita M · CIK 0001811767 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,015.034

F1 · balance_after: Includes shares acquired through reinvestment of quarterly dividends.

SEC source: 0001127602-20-028957 · form4.xml · nonDerivative · entry 1

Rahily Ita M · CIK 0001811767 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,394.271

F1 · shares: Automatic monthly purchase through Tompkins Financial Dividend Reinvestment and Stock Purchase and Sale Plan.

SEC source: 0001127602-20-028709 · form4.xml · nonDerivative · entry 2

GRUBER SCOTT L · CIK 0001481104 · EVP, Pres. & CEO, VIST Bank

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 13,631.182

F2 · shares: Restricted stock was granted pursuant to the Tompkins Financial Corporation 2019 Equity Incentive Plan. Restricted stock grants have a five-year vesting schedule with 0% vesting in year one and 25% vesting in years two through five. The grant will expire ten years from the date of the grant.

SEC source: 0001127602-20-028709 · form4.xml · nonDerivative · entry 1

GRUBER SCOTT L · CIK 0001481104 · EVP, Pres. & CEO, VIST Bank

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 11,876.182

F1 · shares: Deemed disposition of shares to the Issuer to pay for taxes upon vesting of restricted stock.

SEC source: 0001127602-20-028700 · form4.xml · nonDerivative · entry 2

McKenna John M · CIK 0001615770 · EVP, Tompkins Bank of Castile

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 11,970.915

F2 · shares: Restricted stock was granted pursuant to the Tompkins Financial Corporation 2019 Equity Incentive Plan. Restricted stock grants have a five-year vesting schedule with 0% vesting in year one and 25% vesting in years two through five. The grant will expire ten years from the date of the grant.

SEC source: 0001127602-20-028700 · form4.xml · nonDerivative · entry 1

McKenna John M · CIK 0001615770 · EVP, Tompkins Bank of Castile

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 10,215.915

F1 · shares: Deemed disposition of shares to Issuer to satisfy option cost and taxes.

SEC source: 0001127602-20-028711 · form4.xml · nonDerivative · entry 2

Howard Brian A · CIK 0001681102 · EVP, Pres. Tompkins Fin. Adv.

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 6,475.391

F2 · shares: Restricted stock was granted pursuant to the Tompkins Financial Corporation 2019 Equity Incentive Plan. Restricted stock grants have a five-year vesting schedule with 0% vesting in year one and 25% vesting in years two through five. The grant will expire ten years from the date of the grant.

SEC source: 0001127602-20-028711 · form4.xml · nonDerivative · entry 1

Howard Brian A · CIK 0001681102 · EVP, Pres. Tompkins Fin. Adv.

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 4,720.391

F1 · shares: Deemed disposition of shares to the Issuer to pay for taxes upon vesting of restricted stock.

SEC source: 0001127602-20-028752 · form4.xml · nonDerivative · entry 2

Cribbs Steven W · CIK 0001559267 · SVP & Chief Risk Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,405

F2 · shares: Deemed disposition of shares to the Issuer to pay for taxes upon vesting of restricted stock