| 2025 | $1,250.00 | Virtual Ride |
| 2024 | $6,200.63 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $5,061.00 | Reimagined |
| 2022 | $5,404.53 | Wellesley Century |
| 2021 | $6,115.60 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $5,240.20 | Wellesley to Bourne (1-Day, Sat) |
| 2019 | $4,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2018 | $5,525.00 | Wellesley to Provincetown Monument (2-Day) |
| 2017 | $5,875.00 | Wellesley to Provincetown Monument (2-Day) |
| 2016 | $4,500.00 | Wellesley to Provincetown Monument (2-Day) |
| 2015 | $1,000.00 | Wellesley to Wellesley (50 mile Sunday) |
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