| 2025 | $0.00 | Wellesley to Wellesley (50 mile Sunday) and Volunteer |
| $410.00 | PMC Winter Cycle | |
| 2024 | $7,250.00 | Wellesley to Provincetown Inn (2-Day) |
| $400.00 | PMC Winter Cycle | |
| 2023 | $1,950.00 | Wellesley to Wellesley (50 mile Sunday) and Volunteer |
| $500.00 | PMC Winter Cycle | |
| 2022 | $10,000.00 | Wellesley to Patriot Place (25 mile Sunday) and Volunteer |
| $600.00 | PMC Winter Cycle | |
| 2021 | $10,550.00 | Reimagined |
| $100.00 | PMC Winter Cycle | |
| 2020 | $5,750.00 | Bourne to Provincetown Inn (1-Day, Sun) and Volunteer |
| $350.00 | PMC Winter Cycle | |
| 2019 | $0.00 | PMC Volunteer |
