| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $4,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $20,700.00 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $150.00 | PMC Fundraiser |
| 2021 | $9,000.00 | Wellesley to Bourne + Wellesley Century (2-Day) |
| 2020 | $15,190.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $8,600.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $10,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $10,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $11,729.68 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $30,730.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $13,100.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $9,186.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $19,198.00 | Sturbridge to Provincetown Monument (2-Day) |
