| 2025 | $0.00 | Wellesley to Patriot Place (25 mile Sunday) |
| 2024 | $4,505.28 | Wellesley to Patriot Place (25 mile Sunday) |
| 2023 | $5,025.00 | Wellesley Century |
| 2022 | $5,826.00 | Reimagined |
| 2021 | $6,880.00 | Bourne to Provincetown Monument (1-Day, Sun) |
| 2020 | $1,860.00 | Wellesley to Bourne + Wellesley Century (2-Day) |
| 2019 | $1,880.00 | Wellesley to Patriot Place (25 mile Sunday) |
