| 2025 | $0.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2024 | $3,023.12 | Wellesley Century |
| 2023 | $3,362.16 | Wellesley Century |
| 2022 | $4,051.00 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $2,580.18 | Patriot Place to Patriot Place |
| 2020 | $1,160.00 | Wellesley to Patriot Place (25 mile Sunday) |
