| 2025 | $0.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2024 | $2,300.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2023 | $2,000.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2022 | $2,325.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2021 | $2,500.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2019 | $1,000.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2018 | $100.00 | PMC Rider |
| 2017 | $150.00 | PMC Rider |
| 2016 | $3,700.00 | Wellesley to Bourne (1-Day, Sat) |
| 2015 | $1,000.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2014 | $1,000.00 | Wellesley to Wellesley (50 mile Sunday) |
