| Stephanie Oey | $500.00 |
| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $26,710.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $26,015.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $33,853.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $28,495.50 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $24,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $22,874.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $17,961.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $21,191.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $14,730.00 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $10,554.00 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $7,595.00 | Wellesley to Bourne (1-Day, Sat) |
| 2013 | $0.00 | PMC Rider |
| 2012 | $4,300.00 | Wellesley to Provincetown Inn (2-Day) |
| 2011 | $7,760.00 | Wellesley to Bourne (1-Day, Sat) |
| 2010 | $6,851.00 | Wellesley to Provincetown Inn (2-Day) |
| 2009 | $50.00 | PMC Fundraiser |
| 2008 | $4,000.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2007 | $4,362.18 | Sturbridge to Provincetown Inn (2-Day) |
| 2006 | $3,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $4,268.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $3,475.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $2,000.00 | Sturbridge to Wellesley (2-Day) |
