| 2024 | $3,689.01 | Wellesley to Wellesley (50 mile Sunday) |
| 2023 | $4,405.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2022 | $3,915.00 | Wellesley Century |
| 2021 | $4,450.00 | Wellesley to Wellesley (50 mile Sunday) and Volunteer |
| 2020 | $4,451.00 | Wellesley to Wellesley (50 mile Sunday) |
