| 2018 | $0.00 | PMC Rider |
| 2017 | $950.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $0.00 | PMC Rider |
| 2015 | $230.00 | PMC Rider |
| 2014 | $4,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $4,439.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $4,570.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $5,551.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $4,847.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $4,200.34 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $4,486.67 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $5,375.00 | Wellesley to Wellesley (50 mile Sunday) |
