| Mar 8, 2024 | LJLevenson Jonathan B. Group Treasurer | AGrant | 13,448 | — | — | |
| Mar 7, 2024 | BABaker Alexander James Chief Risk Officer | AGrant | 15,778 | — | — | |
| Mar 7, 2024 | DADaws Adrian Joseph CEO, Hamilton Global Specialty | MExercise | 4,608 | — | — | |
| Mar 7, 2024 | KAKuchma Anita Breslin CEO, Hamilton Select | AGrant | 12,069 | — | — | |
| Mar 7, 2024 | DBDeegan Brian John Group Chief Accounting Officer | AGrant | 17,379 | — | — | |
| Mar 7, 2024 | HCHowie Craig Chief Financial Officer | AGrant | 47,586 | — | — | |
| Mar 7, 2024 | FDFisher Daniel Mark Group Head of HR & Comm. | MExercise | 2,469 | — | — | |
| Mar 7, 2024 | CGCarreiro Gemma Elizabeth Group General Counsel | MExercise | 2,673 | — | — | |
| Mar 7, 2024 | BKBernhard Keith Donald Group Chief Audit Officer | AGrant | 9,827 | — | — | |
| Mar 7, 2024 | TMThomas Megan Jane CEO, Hamilton Re | MExercise | 6,020 | — | — | |
| Mar 7, 2024 | AGAlbo Giuseppina Chief Executive Officer | MExercise | 23,480 | — | — | |
| Mar 7, 2024 | KVKrishnamoorthy Venkatanarayanan Group CTO and Group CDO | MExercise | 2,167 | — | — | |
| Mar 5, 2024 | BABaker Alexander James Chief Risk Officer | FTax | 7,585 | $14.95 | $113,396 | |
| Mar 5, 2024 | DADaws Adrian Joseph CEO, Hamilton Global Specialty | FTax | 7,965 | $14.95 | $119,077 | |
| Mar 5, 2024 | KAKuchma Anita Breslin CEO, Hamilton Select | FTax | 1,668 | $14.95 | $24,937 | |
| Mar 5, 2024 | DBDeegan Brian John Group Chief Accounting Officer | MExercise | 13,285 | — | — | |
| Mar 5, 2024 | SESimmons Everard Barclay Director | AGrant | 1,881 | — | — | |
| Mar 5, 2024 | CCCundliffe Chad Allan Group Treasurer | MExercise | 18,315 | — | — | |
| Mar 5, 2024 | HCHowie Craig Chief Financial Officer | FTax | 11,343 | $14.95 | $169,578 | |
| Mar 5, 2024 | BDBROWN DAVID A Chairman of the Board · Director | AGrant | 2,508 | — | — | |
| Mar 5, 2024 | FDFisher Daniel Mark Group Head of HR & Comm. | FTax | 3,893 | $14.95 | $58,200 | |
| Mar 5, 2024 | CGCarreiro Gemma Elizabeth Group General Counsel | MExercise | 9,448 | — | — | |
| Mar 5, 2024 | KA | AGrant | 941 | — | — | |
| Mar 5, 2024 | GJ | AGrant | 941 | — | — | |
| Mar 5, 2024 | BKBernhard Keith Donald Group Chief Audit Officer | MExercise | 9,664 | — | — | |
| Mar 5, 2024 | PM | AGrant | 2,508 | — | — | |
| Mar 5, 2024 | TMThomas Megan Jane CEO, Hamilton Re | MExercise | 31,033 | — | — | |
| Mar 5, 2024 | AGAlbo Giuseppina Chief Executive Officer | FTax | 48,203 | $14.95 | $720,635 | |
| Mar 5, 2024 | RDRichards Doreen Pauline Elizabeth Director | AGrant | 2,508 | — | — | |
| Mar 5, 2024 | FR | AGrant | 3,177 | — | — | |
| Mar 5, 2024 | PSPacala Stephen Wilson Director | AGrant | 2,508 | — | — | |
| Mar 5, 2024 | KVKrishnamoorthy Venkatanarayanan Group CTO and Group CDO | FTax | 2,790 | $14.95 | $41,711 | |
| Mar 5, 2024 | FW | AGrant | 3,411 | — | — | |
| Jan 2, 2024 | TMThomas Megan Jane CEO, Hamilton Re | Holdings only | — | — | — | |
| Jan 2, 2024 | AGAlbo Giuseppina Chief Executive Officer | Holdings only | — | — | — | |
| Jan 2, 2024 | CCCundliffe Chad Allan Group Treasurer | Holdings only | — | — | — | |
| Jan 2, 2024 | DADaws Adrian Joseph CEO, Hamilton Global Specialty | Holdings only | — | — | — | |
| Jan 2, 2024 | HCHowie Craig Group Chief Financial Officer | Holdings only | — | — | — | |
| Jan 2, 2024 | KAKuchma Anita Breslin CEO, Hamilton Select | Holdings only | — | — | — | |
| Jan 2, 2024 | BABaker Alexander James Chief Risk Officer | Holdings only | — | — | — | |
| Jan 2, 2024 | KVKrishnamoorthy Venkatanarayanan Group CTO and Group CDO | Holdings only | — | — | — | |
| Jan 2, 2024 | BKBernhard Keith Donald Group Chief Audit Officer | Holdings only | — | — | — | |
| Jan 2, 2024 | CGCarreiro Gemma Elizabeth Group General Counsel & Sec. | Holdings only | — | — | — | |
| Jan 2, 2024 | FDFisher Daniel Mark Group Head of HR & Comm. | Holdings only | — | — | — | |
| Jan 2, 2024 | DBDeegan Brian John Group Chief Accounting Officer | Holdings only | — | — | — | |