| 2024 | $5,948.00 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $5,867.00 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $4,736.00 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $6,600.00 | Wellesley Century |
| 2020 | $5,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2019 | $4,750.00 | Wellesley to Bourne (1-Day, Sat) |
| 2018 | $4,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2017 | $0.00 | PMC Volunteer |
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