| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $11,020.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $10,240.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $9,749.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $7,105.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2020 | $9,725.00 | Sturbridge to Provincetown Inn (2-Day) |
| $350.00 | PMC Winter Cycle | |
| 2019 | $16,365.00 | Sturbridge to Provincetown Inn (2-Day) |
| $250.00 | PMC Winter Cycle | |
| 2018 | $16,162.25 | Sturbridge to Provincetown Inn (2-Day) |
| $250.00 | PMC Winter Cycle | |
| 2017 | $16,170.00 | Sturbridge to Provincetown Inn (2-Day) |
| $250.00 | The Resolution by PMC | |
| 2016 | $12,305.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $19,351.24 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $16,968.25 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $20,087.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $10,435.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $6,645.00 | Wellesley to Provincetown Inn (2-Day) |
| 2010 | $4,900.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2009 | $3,270.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2008 | $3,155.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2007 | $2,825.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2006 | $50.00 | PMC Volunteer |
| 2005 | $0.00 | PMC Volunteer |
| 2004 | $0.00 | PMC Volunteer |
| 2003 | $0.00 | PMC Volunteer |
| 2002 | $2,260.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2001 | $3,120.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2000 | $3,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1999 | $1,765.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1998 | $1,100.00 | Sturbridge to Provincetown Inn (2-Day) and Volunteer |
| 1997 | $0.00 | PMC Volunteer |
| 1996 | $0.00 | PMC Volunteer |
| 1995 | $0.00 | PMC Volunteer |
| 1994 | $0.00 | PMC Volunteer |
| 1992 | $0.00 | PMC Volunteer |
| 1991 | $0.00 | PMC Volunteer |
| 1989 | $0.00 | PMC Volunteer |
