| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $2,007.26 | Reimagined and Volunteer |
| $2,397.06 | PMC Unpaved | |
| 2023 | $6,543.00 | Sturbridge to Provincetown Inn (2-Day) |
| $1,575.00 | PMC Unpaved | |
| $600.00 | PMC Winter Cycle | |
| 2022 | $1,785.00 | Wellesley to Provincetown Monument (2-Day) and Volunteer |
| $3,300.00 | PMC Unpaved | |
| $1,210.00 | PMC Winter Cycle | |
| 2021 | $2,336.00 | Reimagined and Volunteer |
| $160.00 | PMC Winter Cycle | |
| 2020 | $9,172.99 | Bourne to Provincetown Monument (1-Day, Sun) and Volunteer |
| $1,200.00 | PMC Winter Cycle | |
| 2019 | $700.00 | PMC Virtual Rider and Volunteer |
| $500.00 | PMC Winter Cycle | |
| 2018 | $205.00 | Sturbridge to Provincetown Monument (2-Day) and Volunteer |
| $500.00 | PMC Winter Cycle | |
| 2017 | $2,425.00 | Sturbridge to Provincetown Monument (2-Day) and Volunteer |
| $260.00 | The Resolution by PMC | |
| $5.00 | PMC Winter Cycle | |
| 2016 | $1,428.00 | Sturbridge to Provincetown Monument (2-Day) and Volunteer |
| $0.00 | The Resolution by PMC | |
| 2015 | $1,871.00 | Sturbridge to Provincetown Inn (2-Day) and Volunteer |
| 2014 | $5,020.00 | PMC Virtual Rider and Volunteer |
| 2013 | $531.00 | PMC Virtual Rider and Volunteer |
| 2012 | $3,121.00 | Sturbridge to Provincetown Inn (2-Day) and Volunteer |
| 2011 | $4,281.00 | Bourne to Wellesley (1-Day, Sun) and Volunteer |
| 2010 | $4,038.00 | PMC Virtual Rider and Volunteer |
| 2009 | $1,000.00 | PMC Virtual Rider and Volunteer |
| 2008 | $4,202.00 | Sturbridge to Wellesley (2-Day) and Volunteer |
| 2007 | $3,336.98 | PMC Virtual Rider and Volunteer |
| 2006 | $2,134.07 | Sturbridge to Provincetown Inn (2-Day) and Volunteer |
| 2005 | $1,410.00 | Bourne to Wellesley (1-Day, Sun) and Volunteer |
| 2004 | $2,836.63 | Sturbridge to Provincetown Inn (2-Day) and Volunteer |
| 2003 | $5,538.32 | Sturbridge to Provincetown Inn (2-Day) and Volunteer |
| 2002 | $4,110.00 | PMC Virtual Rider and Volunteer |
| 2001 | $3,600.00 | PMC Virtual Rider and Volunteer |
| 2000 | $2,508.00 | Wellesley to Wellesley (2-Day) |
| 1999 | $2,600.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1998 | $1,975.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1997 | $2,000.00 | PMC Rider |
| 1996 | $2,000.00 | PMC Rider |
| 1995 | $100.00 | PMC Rider |
| 1994 | $2,125.00 | PMC Rider |
| 1993 | $2,150.00 | PMC Rider |
| 1992 | $2,175.00 | PMC Rider |
| 1991 | $2,100.00 | PMC Rider |
| 1990 | $2,125.00 | PMC Rider |
