Bentley Raymond B.

SEC source: 0001104659-26-112873 · tm2625908-10_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 14,816,404

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

SEC source: 0001104659-26-074058 · tm2614939-13_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 14,814,360

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

SEC source: 0001104659-26-033331 · tm268358-28_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 14,812,284

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

SEC source: 0001104659-26-028471 · tm268358-9_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 14,810,613

SEC source: 0001104659-26-005040 · tm2534084-5_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 15,060,613

F1 · kind: Represents shares of Class B Common Stock withheld by the Issuer to cover taxes due by the Reporting Person upon a scheduled distribution of Class B Common Stock from the Issuer's Non-Qualified Deferred Compensation Plan.

SEC source: 0001104659-25-121164 · tm2532204-12_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 15,103,583

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

SEC source: 0001104659-25-120662 · tm2532204-2_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 15,101,853

SEC source: 0001104659-25-096084 · tm2526753-10_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 15,348,804

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

SEC source: 0001104659-25-061676 · tm2518160-2_4seq1.xml · nonDerivative · entry 3

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 15,347,424

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on March 13, 2025.

F4 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on June 20, 2025 at prices ranging from $50.375 to $51.16. The Reporting Person undertakes to provide to Bentley Systems, Incorporated, any security holder of Bentley Systems, Incorporated, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-25-061676 · tm2518160-2_4seq1.xml · nonDerivative · entry 2

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 15,469,538

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on March 13, 2025.

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on June 18, 2025 at prices ranging from $50.97 to $50.985. The Reporting Person undertakes to provide to Bentley Systems, Incorporated, any security holder of Bentley Systems, Incorporated, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-25-061676 · tm2518160-2_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 15,471,938

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on March 13, 2025.

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on June 18, 2025 at prices ranging from $49.96 to $50.96. The Reporting Person undertakes to provide to Bentley Systems, Incorporated, any security holder of Bentley Systems, Incorporated, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-25-060641 · tm2518160-1_4seq1.xml · nonDerivative · entry 2

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 15,719,227

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on March 13, 2025.

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on June 17, 2025 at prices ranging from $49.805 to $50.52. The Reporting Person undertakes to provide to Bentley Systems, Incorporated, any security holder of Bentley Systems, Incorporated, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-25-060641 · tm2518160-1_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 15,992,321

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on March 13, 2025.

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on June 16, 2025 at prices ranging from $49.33 to $50.145. The Reporting Person undertakes to provide to Bentley Systems, Incorporated, any security holder of Bentley Systems, Incorporated, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-25-059888 · tm2515831-14_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 16,347,424

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

SEC source: 0001104659-25-029886 · tm259640-10_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 16,345,982

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

SEC source: 0001104659-24-128920 · tm2431080-9_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 16,344,228

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

SEC source: 0001104659-24-104294 · tm2425147-9_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 16,342,832

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

SEC source: 0001104659-24-098147 · tm2423571-1_4seq1.xml · nonDerivative · entry 4

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 16,341,504

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on May 23, 2024.

SEC source: 0001104659-24-098147 · tm2423571-1_4seq1.xml · nonDerivative · entry 3

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 16,341,514

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on May 23, 2024.

F4 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on September 6, 2024 at prices ranging from $47.925 to 48.92. The Reporting Person undertakes to provide to Bentley Systems, Incorporated, any security holder of Bentley Systems, Incorporated, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-24-098147 · tm2423571-1_4seq1.xml · nonDerivative · entry 2

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 16,407,000

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on May 23, 2024.

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on September 5, 2024 at prices ranging from $48.735 to $48.805. The Reporting Person undertakes to provide to Bentley Systems, Incorporated, any security holder of Bentley Systems, Incorporated, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-24-098147 · tm2423571-1_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 16,410,561

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on May 23, 2024.

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on September 5, 2024 at prices ranging from $47.735 to $48.73. The Reporting Person undertakes to provide to Bentley Systems, Incorporated, any security holder of Bentley Systems, Incorporated, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-24-097451 · tm2423412-1_4seq1.xml · nonDerivative · entry 4

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 16,494,397

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on May 23, 2024.

F5 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on September 4, 2024 at prices ranging from $48.01 to $48.8050. The Reporting Person undertakes to provide to Bentley Systems, Incorporated, any security holder of Bentley Systems, Incorporated, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-24-097451 · tm2423412-1_4seq1.xml · nonDerivative · entry 3

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 16,598,656

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on May 23, 2024.

F4 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on September 3, 2024 at prices ranging from $50.68 to $51.33. The Reporting Person undertakes to provide to Bentley Systems, Incorporated, any security holder of Bentley Systems, Incorporated, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-24-097451 · tm2423412-1_4seq1.xml · nonDerivative · entry 2

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 16,601,326

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on May 23, 2024.

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on September 3, 2024 at prices ranging from $49.66 to $50.63. The Reporting Person undertakes to provide to Bentley Systems, Incorporated, any security holder of Bentley Systems, Incorporated, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-24-097451 · tm2423412-1_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 16,629,204

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on May 23, 2024.

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on September 3, 2024 at prices ranging from $48.655 to $49.65. The Reporting Person undertakes to provide to Bentley Systems, Incorporated, any security holder of Bentley Systems, Incorporated, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-24-096371 · tm2423185-1_4seq1.xml · nonDerivative · entry 2

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 16,689,701

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on May 23, 2024.

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on August 30, 2024 at prices ranging from $51.32 to $51.97. The Reporting Person undertakes to provide to Bentley Systems, Incorporated, any security holder of Bentley Systems, Incorporated, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-24-096371 · tm2423185-1_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 16,820,525

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on May 23, 2024.

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on August 29, 2024 at prices ranging from $50.89 to $51.86. The Reporting Person undertakes to provide to Bentley Systems, Incorporated, any security holder of Bentley Systems, Incorporated, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-24-072296 · tm2417202-6_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 16,941,504

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

SEC source: 0001104659-24-066655 · tm2415812-1_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 16,940,172

SEC source: 0001104659-24-041955 · tm247953-19_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 17,190,172

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

SEC source: 0001104659-23-126947 · tm2333034-2_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 17,188,887

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

SEC source: 0001104659-23-096031 · tm2322724-10_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 17,187,798

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

SEC source: 0001104659-23-073772 · tm2317958-10_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 17,186,599

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

SEC source: 0001104659-23-030634 · tm238296-12_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 17,185,547

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

SEC source: 0001104659-22-126307 · tm2232398-10_4seq1.xml · nonDerivative · entry 2

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 17,184,156

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

SEC source: 0001104659-22-126307 · tm2232398-10_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 17,183,309

SEC source: 0001104659-22-100838 · tm2225081-11_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 17,335,699

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

SEC source: 0001104659-22-074781 · tm2219427-9_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 17,334,753

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

SEC source: 0001104659-22-052614 · tm2213180-10_4seq1.xml · nonDerivative · entry 6

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 17,333,785

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on March 14, 2022.

F7 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on April 28, 2022 at prices ranging from $42.61 to $42.63. The reporting person undertakes to provide to Bentley Systems, Incorporated, any security holder of Bentley Systems, Incorporated, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-22-052614 · tm2213180-10_4seq1.xml · nonDerivative · entry 5

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 17,340,009

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on March 14, 2022.

F6 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on April 28, 2022 at prices ranging from $41.61 to $42.605. The reporting person undertakes to provide to Bentley Systems, Incorporated, any security holder of Bentley Systems, Incorporated, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-22-052614 · tm2213180-10_4seq1.xml · nonDerivative · entry 4

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 17,386,870

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on March 14, 2022.

F5 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on April 27, 2022 at prices ranging from $41.935 to $42.41. The reporting person undertakes to provide to Bentley Systems, Incorporated, any security holder of Bentley Systems, Incorporated, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-22-052614 · tm2213180-10_4seq1.xml · nonDerivative · entry 3

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 17,422,071

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on March 14, 2022.

F4 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on April 27, 2022 at prices ranging from $40.935 to $41.93. The reporting person undertakes to provide to Bentley Systems, Incorporated, any security holder of Bentley Systems, Incorporated, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-22-052614 · tm2213180-10_4seq1.xml · nonDerivative · entry 2

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 17,516,906

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on March 14, 2022.

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on April 26, 2022 at prices ranging from $42.385 to $42.99. The reporting person undertakes to provide to Bentley Systems, Incorporated, any security holder of Bentley Systems, Incorporated, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-22-052614 · tm2213180-10_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 17,523,759

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on March 14, 2022.

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on April 26, 2022 at prices ranging from $41.385 to $42.36. The reporting person undertakes to provide to Bentley Systems, Incorporated, any security holder of Bentley Systems, Incorporated, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-22-050378 · tm2213180-9_4seq1.xml · nonDerivative · entry 5

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 17,647,285

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on March 14, 2022.

F6 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on April 25, 2022 at prices ranging from $43.3600 to $43.4000. The reporting person undertakes to provide to Bentley Systems, Incorporated, any security holder of Bentley Systems, Incorporated, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-22-050378 · tm2213180-9_4seq1.xml · nonDerivative · entry 4

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 17,651,426

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on March 14, 2022.

F5 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on April 25, 2022 at prices ranging from $42.3600 to $43.3500. The reporting person undertakes to provide to Bentley Systems, Incorporated, any security holder of Bentley Systems, Incorporated, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-22-050378 · tm2213180-9_4seq1.xml · nonDerivative · entry 3

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 17,786,276

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on March 14, 2022.

F4 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on April 25, 2022 at prices ranging from $41.3600 to $42.3550. The reporting person undertakes to provide to Bentley Systems, Incorporated, any security holder of Bentley Systems, Incorporated, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-22-050378 · tm2213180-9_4seq1.xml · nonDerivative · entry 2

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 17,860,832

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on March 14, 2022.

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on April 22, 2022 at prices ranging from $43.0100 to $43.9600. The reporting person undertakes to provide to Bentley Systems, Incorporated, any security holder of Bentley Systems, Incorporated, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-22-050378 · tm2213180-9_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 17,886,145

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on March 14, 2022.

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on April 22, 2022 at prices ranging from $42.0100 to $43.0000. The reporting person undertakes to provide to Bentley Systems, Incorporated, any security holder of Bentley Systems, Incorporated, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001104659-22-049053 · tm2213180-8_4seq1.xml · nonDerivative · entry 4

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 17,965,172

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on March 14, 2022.

F5 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on April 21, 2022 at prices ranging from $44.0600 to $45.0250. The reporting person undertakes to provide to Bentley Systems, Incorporated, any security holder of Bentley Systems, Incorporated, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.