






| Jon Tepper | $72.00 | 
| Chris Wraight | 
| 2025 | $739.62 | PMC Volunteer | 
| $6,463.00 | PMC Unpaved | |
| 2024 | $119.43 | PMC Volunteer | 
| $6,050.00 | PMC Unpaved | |
| 2023 | $0.00 | PMC Volunteer | 
| $6,353.00 | PMC Unpaved | |
| 2022 | $3,116.00 | PMC Volunteer | 
| 2021 | $3,128.00 | Reimagined | 
| 2020 | $3,736.00 | Wellesley to Wellesley (50 mile Sunday) and Volunteer | 
| 2019 | $9,585.00 | PMC Virtual Rider and Volunteer | 
| 2018 | $5,611.00 | Wellesley to Provincetown Inn (2-Day) | 
| 2017 | $8,560.00 | Wellesley to Provincetown Inn (2-Day) | 
| 2016 | $8,129.00 | Wellesley to Provincetown Inn (2-Day) | 
| 2015 | $10,414.75 | Wellesley to Provincetown Inn (2-Day) | 
| 2014 | $7,399.00 | Wellesley to Provincetown Inn (2-Day) | 
| 2013 | $9,171.00 | Wellesley to Provincetown Inn (2-Day) | 
| 2012 | $7,608.00 | Wellesley to Provincetown Inn (2-Day) | 
| 2011 | $6,575.01 | Wellesley to Provincetown Inn (2-Day) | 
| 2010 | $4,607.00 | Wellesley to Provincetown Inn (2-Day) | 
| 2009 | $6,056.00 | Wellesley to Provincetown Inn (2-Day) | 
| 2008 | $6,973.00 | Wellesley to Provincetown Inn (2-Day) | 
| 2007 | $8,993.00 | Wellesley to Provincetown Inn (2-Day) | 
| 2006 | $9,414.00 | Wellesley to Provincetown Inn (2-Day) | 
| 2005 | $8,016.00 | Wellesley to Provincetown Inn (2-Day) | 
| 2004 | $6,190.00 | Wellesley to Provincetown Inn (2-Day) | 
| 2003 | $5,030.00 | Wellesley to Provincetown Inn (2-Day) | 
| 2002 | $4,716.00 | Wellesley to Provincetown Inn (2-Day) | 
| 2001 | $3,867.00 | Wellesley to Provincetown Inn (2-Day) | 
| 2000 | $2,748.00 | Wellesley to Provincetown Inn (2-Day) | 
| 1999 | $1,647.00 | Wellesley to Provincetown Inn (2-Day) | 
| 1998 | $1,258.00 | Sturbridge to Provincetown Inn (2-Day) |