| 2025 | $0.00 | PMC |
| 2024 | $3,288.00 | Reimagined and Volunteer |
| 2023 | $3,055.00 | Reimagined and Volunteer |
| 2022 | $3,250.00 | Wellesley to Patriot Place (25 mile Sunday) |
| 2021 | $3,237.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2020 | $4,217.40 | Wellesley to Bourne (1-Day, Sat) |
| 2019 | $4,017.10 | Wellesley to Bourne (1-Day, Sat) |
| 2018 | $4,030.00 | Wellesley to Bourne (1-Day, Sat) |
| 2017 | $7,800.00 | Wellesley to Bourne (1-Day, Sat) |
| 2011 | $0.00 | PMC Volunteer |
