| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $18,907.65 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $15,350.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $13,520.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $16,705.00 | Wellesley Century |
| 2020 | $14,726.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $12,966.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $15,280.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $13,442.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $16,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $15,420.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $12,310.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $14,188.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $15,520.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $12,055.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $12,010.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $11,469.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $10,460.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $16,675.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2006 | $12,660.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $10,610.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $11,850.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $11,464.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2002 | $13,581.20 | Sturbridge to Provincetown Inn (2-Day) |
| 2001 | $15,150.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2000 | $6,582.40 | Sturbridge to Provincetown Inn (2-Day) |
| 1999 | $2,576.20 | Sturbridge to Provincetown Inn (2-Day) |
| 1998 | $7,558.50 | Sturbridge to Provincetown Inn (2-Day) |
| 1997 | $5,290.00 | PMC Rider |
| 1996 | $2,527.00 | PMC Rider |
| 1995 | $2,001.00 | PMC Rider |
| 1994 | $1,967.00 | PMC Rider |
