| 2025 | $0.00 | Bourne to Provincetown Inn (1-Day, Sun) |
| 2024 | $7,891.00 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $5,770.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2022 | $7,245.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2021 | $8,405.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2020 | $1,500.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2019 | $4,192.70 | Wellesley to Wellesley (50 mile Sunday) |
