| 2025 | $0.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2024 | $3,180.00 | Wellesley Century |
| 2023 | $3,690.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2022 | $6,154.00 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $2,155.00 | Patriot Place to Patriot Place |
| 2020 | $890.00 | Wellesley to Wellesley (50 mile Sunday) and Volunteer |
| 2019 | $1,320.00 | Wellesley to Wellesley (50 mile Sunday) |
