| John Leite |
| 2025 | $50.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $20,367.00 | Wellesley Century |
| 2023 | $14,262.00 | Bourne to Provincetown Inn (1-Day, Sun) |
| 2022 | $13,804.20 | Bourne to Provincetown Monument (1-Day, Sun) |
| 2021 | $11,005.50 | Wellesley to Wellesley (50 mile Sunday) |
