| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $8,130.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $7,239.07 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $6,600.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $6,828.00 | Wellesley Century |
| 2020 | $1,921.00 | Wellesley to Provincetown Inn (2-Day) |
| $350.00 | PMC Winter Cycle | |
| 2018 | $13,996.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $10,163.73 | Wellesley to Wellesley (50 mile Sunday) |
| 2016 | $4,500.00 | Wellesley to Provincetown Inn (2-Day) |
