| 2025 | $0.00 | PMC |
| 2024 | $250.00 | PMC Fundraiser |
| 2023 | $3,547.50 | Wellesley to Wellesley (50 mile Sunday) |
| 2022 | $6,100.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $2,790.00 | Reimagined |
| 2020 | $1,528.00 | PMC Rider |
| 2019 | $8,625.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $5,390.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $7,900.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $5,880.00 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $4,720.00 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $3,200.00 | Wellesley to Bourne (1-Day, Sat) |
| 2004 | $2,798.00 | Wellesley to Provincetown Inn (2-Day) |
| 2003 | $2,666.00 | Wellesley to Provincetown Inn (2-Day) |
| 2001 | $3,600.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2000 | $3,000.00 | Sturbridge to Provincetown Inn (2-Day) |
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