| 2025 | $0.00 | Wellesley to Provincetown Monument (2-Day) |
| $0.00 | PMC Unpaved | |
| 2024 | $10,000.00 | Wellesley to Provincetown Monument (2-Day) |
| $2,000.00 | PMC Unpaved | |
| 2023 | $10,000.00 | Wellesley to Provincetown Monument (2-Day) |
| $2,000.00 | PMC Unpaved | |
| 2022 | $9,500.00 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $9,692.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $4,627.00 | Wellesley to Provincetown Monument (2-Day) |
| $405.00 | PMC Winter Cycle | |
| 2019 | $8,500.51 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $8,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2017 | $4,816.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $5,019.00 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $7,200.38 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $6,908.69 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $6,700.00 | Wellesley to Provincetown Inn (2-Day) |
| 2012 | $4,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $5,095.00 | Sturbridge to Provincetown Monument (2-Day) |
