| 2025 | $250.00 | Bourne to Provincetown Inn (1-Day, Sun) |
| 2024 | $7,611.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $8,116.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $6,512.87 | Wellesley Century |
| 2021 | $4,490.00 | Wellesley Century |
| 2020 | $6,295.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $6,685.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $6,475.00 | Wellesley to Bourne + Wellesley Century (2-Day) |
| 2017 | $5,270.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $7,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $5,890.00 | Wellesley to Wellesley (2-Day) |
| 2014 | $4,825.00 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $5,290.00 | Wellesley to Provincetown Inn (2-Day) |
| 2012 | $4,605.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $4,100.00 | Wellesley to Wellesley (2-Day) |
| 2010 | $4,080.00 | Wellesley to Wellesley (2-Day) |
| 2009 | $4,160.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2008 | $3,400.00 | Wellesley to Wellesley (2-Day) |
| 2007 | $3,390.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2006 | $6,001.00 | Wellesley to Wellesley (2-Day) |
| 2005 | $12,140.00 | Sturbridge to Wellesley (2-Day) |
| 2004 | $5,500.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2003 | $3,395.00 | Wellesley to Wellesley (2-Day) |
| 2002 | $3,105.00 | Wellesley to Wellesley (2-Day) |
| 2001 | $4,390.00 | Wellesley to Wellesley (2-Day) |
| 2000 | $4,150.00 | Wellesley to Wellesley (2-Day) |
| 1999 | $1,300.00 | Wellesley to Wellesley (2-Day) |
| 1998 | $1,100.00 | Wellesley to Wellesley (2-Day) |
| 1997 | $695.00 | PMC Rider |
| 1996 | $1,015.00 | PMC Rider |
| 1995 | $1,000.00 | PMC Rider |
| 1994 | $65.00 | PMC Rider |
