| 2025 | $0.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2024 | $2,050.00 | Wellesley to Patriot Place (25 mile Sunday) |
| 2023 | $6,186.00 | Wellesley to Provincetown Monument (2-Day) |
| 2022 | $3,161.00 | Wellesley Century |
| 2021 | $3,751.00 | Reimagined |
| 2020 | $3,250.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $8,500.00 | Wellesley to Provincetown Monument (2-Day) |
