| Gregory Shea | $50.00 |
| 2025 | $50.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $7,824.65 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $7,712.00 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $6,292.00 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $6,132.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2020 | $7,125.00 | Wellesley to Bourne (1-Day, Sat) |
| 2019 | $6,547.00 | Wellesley to Bourne (1-Day, Sat) |
| 2018 | $5,072.00 | Wellesley to Bourne (1-Day, Sat) |
| 2017 | $6,297.00 | Wellesley to Bourne (1-Day, Sat) |
| 2016 | $5,792.00 | Wellesley to Bourne (1-Day, Sat) |
| 2015 | $4,538.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $3,200.00 | Wellesley to Bourne (1-Day, Sat) |
| 2012 | $4,367.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $4,327.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $5,058.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $4,950.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $4,050.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $3,775.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2006 | $3,375.00 | Sturbridge to Provincetown Inn (2-Day) |
