| 2024 | $7,908.22 | Wellesley to Wellesley (50 mile Sunday) |
| 2023 | $3,425.00 | Wellesley to Wellesley (50 mile Sunday) and Volunteer |
| 2022 | $3,650.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2021 | $2,030.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2020 | $1,000.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2019 | $1,150.00 | Wellesley to Wellesley (50 mile Sunday) |
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