| 2025 | $0.00 | Wellesley to Patriot Place (25 mile Sunday) |
| $400.00 | PMC Winter Cycle | |
| 2024 | $2,000.00 | Wellesley to Patriot Place (25 mile Sunday) |
| $400.00 | PMC Winter Cycle | |
| 2023 | $0.00 | Virtual Ride |
| 2022 | $2,150.00 | Wellesley to Patriot Place (25 mile Sunday) |
| 2021 | $500.55 | PMC Winter Cycle |
| 2020 | $0.00 | Wellesley to Bourne (1-Day, Sat) |
| 2019 | $1,260.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2018 | $5,027.93 | Wellesley to Bourne (1-Day, Sat) |
| 2017 | $1,810.04 | Wellesley to Patriot Place (25 mile Sunday) |
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