| MATTHEW JAMIESON | $50.00 |
| 2025 | $260.00 | PMC Fundraiser |
| 2024 | $1,100.00 | PMC Fundraiser |
| 2023 | $8,417.46 | Wellesley to Wellesley (50 mile Sunday) |
| 2022 | $9,579.13 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $8,222.25 | Wellesley to Wellesley (50 mile Sunday) |
| 2020 | $7,134.55 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $9,468.83 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $9,956.77 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $6,687.25 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $6,449.97 | Wellesley to Provincetown Monument (2-Day) |
| 2015 | $7,100.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2014 | $9,373.04 | Sturbridge to Provincetown Monument (2-Day) |
| 2013 | $8,740.61 | Sturbridge to Provincetown Monument (2-Day) |
| 2012 | $10,170.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2011 | $7,805.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2010 | $6,905.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2009 | $7,892.00 | Wellesley to Wellesley (50 mile Sunday) |
