| 2025 | $0.00 | Wellesley to Bourne (1-Day, Sat) |
| $0.00 | PMC Winter Cycle | |
| 2024 | $10,568.00 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $11,430.00 | Wellesley to Bourne + Wellesley to Wellesley |
| 2022 | $6,175.00 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $4,202.00 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $4,710.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $5,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $5,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $4,980.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $3,700.00 | Wellesley to Bourne (1-Day, Sat) |
| 2015 | $3,500.00 | Wellesley to Bourne (1-Day, Sat) |
| 2014 | $3,709.89 | Wellesley to Bourne (1-Day, Sat) |
| 2013 | $3,946.09 | Wellesley to Bourne (1-Day, Sat) |
| 2012 | $4,400.00 | Wellesley to Provincetown Inn (2-Day) |
| 2011 | $3,730.00 | Wellesley to Bourne (1-Day, Sat) |
| 2010 | $3,010.00 | Wellesley to Bourne (1-Day, Sat) |
| 2009 | $3,150.00 | Wellesley to Bourne (1-Day, Sat) |
| 2008 | $3,025.00 | Wellesley to Bourne (1-Day, Sat) |
| 2007 | $3,210.00 | Wellesley to Bourne (1-Day, Sat) |
| 2006 | $3,600.00 | Wellesley to Bourne (1-Day, Sat) |
| 2005 | $3,625.00 | Wellesley to Bourne (1-Day, Sat) |
| 2004 | $2,820.00 | Wellesley to Bourne (1-Day, Sat) |
| 2003 | $2,605.00 | Wellesley to Bourne (1-Day, Sat) |
| 2002 | $2,370.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2001 | $1,800.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2000 | $3,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1999 | $2,600.00 | Sturbridge to Wellesley (2-Day) |
| 1998 | $2,632.50 | Sturbridge to Provincetown Inn (2-Day) |
| 1997 | $2,015.00 | PMC Rider |
| 1996 | $2,000.00 | PMC Rider |
