| 2020 | $60.00 | PMC Fundraiser |
| 2019 | $75.00 | PMC Fundraiser |
| 2018 | $200.00 | PMC Rider |
| 2017 | $1,470.00 | Wellesley to Patriot Place (25 mile Sunday) |
| 2016 | $1,555.00 | Wellesley to Patriot Place (25 mile Sunday) |
| 2015 | $1,925.00 | Wellesley to Patriot Place (25 mile Sunday) |
| 2014 | $2,100.00 | Wellesley to Patriot Place (25 mile Sunday) |
| 2013 | $2,745.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2012 | $4,427.13 | Wellesley to Provincetown Inn (2-Day) |
| 2011 | $4,200.00 | Wellesley to Provincetown Inn (2-Day) |
| 2010 | $2,795.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2009 | $2,821.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2008 | $4,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2007 | $7,425.00 | Wellesley to Provincetown Inn (2-Day) |
| 2006 | $3,370.00 | Wellesley to Provincetown Inn (2-Day) |
| 2005 | $3,200.00 | Wellesley to Provincetown Inn (2-Day) |
| 2004 | $2,800.00 | Wellesley to Provincetown Inn (2-Day) |
| 2003 | $2,500.00 | Wellesley to Provincetown Inn (2-Day) |
| 2002 | $1,150.00 | Wellesley to Bourne (1-Day, Sat) |
| 2001 | $1,800.00 | Wellesley to Provincetown Inn (2-Day) |
| 2000 | $1,650.00 | Wellesley to Provincetown Inn (2-Day) |
| 1999 | $1,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 1998 | $1,755.00 | Wellesley to Provincetown Inn (2-Day) |
