| 2025 | $0.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2024 | $2,564.94 | Reimagined |
| 2023 | $2,000.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2022 | $2,051.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2021 | $2,000.00 | Patriot Place to Patriot Place |
| 2020 | $0.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2019 | $1,669.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2017 | $2,008.50 | Wellesley to Wellesley (50 mile Sunday) |
