| 2025 | $0.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $6,149.51 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $4,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $4,050.00 | Wellesley to Patriot Place (25 mile Sunday) |
| 2021 | $6,255.10 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $2,613.94 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $5,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $6,011.00 | Wellesley to Wellesley (2-Day) |
| $250.00 | PMC Winter Cycle | |
| 2017 | $7,800.00 | Wellesley to Provincetown Monument (2-Day) |
| 2015 | $4,500.00 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $5,425.00 | Wellesley to Provincetown Monument (2-Day) |
| 2013 | $4,300.00 | Wellesley to Provincetown Inn (2-Day) |
| 2012 | $4,751.00 | Wellesley to Provincetown Monument (2-Day) |
