| 2025 | $617.56 | PMC Winter Cycle |
| 2024 | $6,058.52 | Wellesley to Provincetown Monument (2-Day) |
| $0.00 | PMC Unpaved | |
| $624.00 | PMC Winter Cycle | |
| 2023 | $1,564.00 | PMC Winter Cycle |
| 2022 | $10,198.00 | Wellesley to Provincetown Monument (2-Day) |
| $600.00 | PMC Winter Cycle | |
| 2021 | $4,175.00 | PMC Winter Cycle |
| 2020 | $9,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| $350.00 | PMC Winter Cycle | |
| 2019 | $9,462.48 | Sturbridge to Provincetown Monument (2-Day) |
| $250.00 | PMC Winter Cycle |
