| 2024 | $6,654.15 | Wellesley to Wellesley (50 mile Sunday) |
| 2023 | $6,520.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2022 | $6,090.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2021 | $8,220.00 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $5,518.00 | Wellesley to Bourne (1-Day, Sat) |
| 2019 | $6,660.89 | Wellesley to Bourne (1-Day, Sat) |
| 2018 | $4,880.00 | Wellesley to Wellesley (50 mile Sunday) and Volunteer |
| 2017 | $3,425.00 | Wellesley to Wellesley (50 mile Sunday) and Volunteer |
| 2016 | $4,080.00 | Wellesley to Wellesley (50 mile Sunday) and Volunteer |
| 2014 | $0.00 | PMC Volunteer |
