| 2025 | $0.00 | PMC |
| $950.00 | PMC Winter Cycle | |
| 2024 | $3,907.92 | Reimagined and Volunteer |
| $1,500.00 | PMC Unpaved | |
| 2023 | $10,018.55 | Sturbridge to Provincetown Inn (2-Day) |
| $1,500.00 | PMC Unpaved | |
| 2022 | $11,087.97 | Sturbridge to Provincetown Inn (2-Day) |
| $0.00 | PMC Unpaved | |
| 2021 | $10,215.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2020 | $7,830.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2019 | $8,705.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2018 | $5,150.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2017 | $5,433.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2016 | $5,175.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2015 | $4,060.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2014 | $3,569.89 | Sturbridge to Bourne (1-Day, Sat) |
| 2013 | $4,751.09 | Sturbridge to Bourne (1-Day, Sat) |
| 2012 | $4,027.50 | Sturbridge to Bourne (1-Day, Sat) |
| 2011 | $2,500.00 | Bourne to Wellesley (1-Day, Sun) and Volunteer |
| 2010 | $780.00 | PMC Virtual Rider and Volunteer |
| 2009 | $1,040.00 | Bourne to Wellesley (1-Day, Sun) and Volunteer |
| 2008 | $4,250.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $4,120.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2006 | $4,165.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $4,235.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $3,210.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $3,680.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2002 | $3,396.00 | Wellesley to Provincetown Inn (2-Day) |
| 2001 | $2,900.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2000 | $3,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1999 | $1,670.00 | Wellesley to Bourne (1-Day, Sat) |
