| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $8,225.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $7,957.10 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $7,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $8,272.00 | Wellesley Century |
| 2020 | $6,298.68 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $6,880.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $6,625.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $5,755.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $6,075.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $4,895.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $4,337.68 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $4,543.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $7,096.11 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $6,910.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $4,230.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $4,570.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $10,664.00 | Sturbridge to Provincetown Inn (2-Day) and Volunteer |
| 2007 | $5,625.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2006 | $4,027.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $4,277.00 | Wellesley to Provincetown Inn (2-Day) |
| 2004 | $2,980.00 | Wellesley to Provincetown Inn (2-Day) |
| 2003 | $2,790.00 | Wellesley to Provincetown Inn (2-Day) |
| 2002 | $3,280.00 | Wellesley to Provincetown Inn (2-Day) |
| 2001 | $1,355.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2000 | $3,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1999 | $565.00 | PMC Volunteer |
| 1998 | $2,535.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1997 | $2,006.00 | PMC Rider |
| 1996 | $1,635.00 | PMC Rider |
| 1995 | $2,008.00 | PMC Rider |
