| 2025 | $0.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $2,000.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2022 | $6,505.50 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $3,568.00 | Wellesley Century |
| 2020 | $1,971.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $5,935.00 | Wellesley to Provincetown Inn (2-Day) |
