| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| $0.00 | PMC Winter Cycle | |
| 2024 | $6,001.00 | Wellesley to Provincetown Inn (2-Day) |
| $4,001.00 | PMC Unpaved | |
| $0.00 | PMC Winter Cycle | |
| 2023 | $6,000.00 | Wellesley to Provincetown Monument (2-Day) |
| $4,125.00 | PMC Unpaved | |
| 2022 | $2,075.25 | PMC Unpaved |
| 2020 | $1,167.00 | Wellesley to Wellesley (50 mile Sunday) |
