| 2025 | $250.00 | PMC Unpaved |
| 2024 | $0.00 | PMC |
| $4,746.00 | PMC Unpaved | |
| 2023 | $2,832.00 | PMC Unpaved |
| 2022 | $4,045.00 | PMC Unpaved |
| 2021 | $4,925.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2020 | $1,755.00 | Wellesley to Bourne (1-Day, Sat) |
| 2019 | $2,161.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2018 | $1,790.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2017 | $1,415.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2016 | $1,375.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2015 | $4,500.00 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $5,250.00 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $6,100.00 | Wellesley to Provincetown Inn (2-Day) |
| 2012 | $4,300.00 | Wellesley to Provincetown Inn (2-Day) |
| 2011 | $4,250.00 | Wellesley to Provincetown Inn (2-Day) |
| 2010 | $5,315.00 | Wellesley to Provincetown Inn (2-Day) |
| 2008 | $6,625.00 | Wellesley to Provincetown Inn (2-Day) |
| 2007 | $3,870.00 | Wellesley to Bourne (1-Day, Sat) |
| 2006 | $5,212.50 | Wellesley to Provincetown Inn (2-Day) |
| 2005 | $5,235.00 | Wellesley to Provincetown Inn (2-Day) |
| 2004 | $4,145.00 | Wellesley to Provincetown Inn (2-Day) |
| 2003 | $2,793.00 | Sturbridge to Provincetown Inn (2-Day) |
