| 2024 | $5,015.55 | Wellesley to Wellesley (50 mile Sunday) |
| 2023 | $5,270.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2022 | $6,238.54 | Wellesley Century |
| 2021 | $6,500.00 | Wellesley Century |
| 2020 | $9,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $8,504.20 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $5,135.00 | Wellesley to Provincetown Inn (2-Day) |
