| 2025 | $200.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $11,279.89 | Wellesley to Bourne (1-Day, Sat) |
| $1,530.00 | PMC Unpaved | |
| 2023 | $10,480.78 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $11,268.16 | Wellesley Century |
| 2021 | $11,283.60 | Reimagined |
| 2020 | $11,125.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $10,444.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $12,561.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $8,348.70 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $9,853.00 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $10,656.25 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $9,517.00 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $13,252.00 | Wellesley to Provincetown Inn (2-Day) |
| 2012 | $9,060.00 | Wellesley to Provincetown Inn (2-Day) |
| 2011 | $6,464.00 | Wellesley to Provincetown Inn (2-Day) |
| 2010 | $7,570.00 | Wellesley to Provincetown Inn (2-Day) |
| 2009 | $6,007.13 | Wellesley to Wellesley (2-Day) |
| 2008 | $5,333.00 | Wellesley to Provincetown Inn (2-Day) |
| 2007 | $5,791.00 | Wellesley to Wellesley (2-Day) |
| 2006 | $5,136.00 | Wellesley to Provincetown Inn (2-Day) |
| 2005 | $3,973.00 | Wellesley to Wellesley (2-Day) |
| 2004 | $3,364.00 | Wellesley to Wellesley (2-Day) |
| 2003 | $2,749.00 | Wellesley to Wellesley (2-Day) |
| 2001 | $3,709.00 | Wellesley to Wellesley (2-Day) |
| 2000 | $3,052.00 | Wellesley to Wellesley (2-Day) |
| 1999 | $0.00 | PMC |
| 1998 | $36.00 | PMC Fundraiser |
| 1997 | $2,364.00 | PMC Rider |
| 1996 | $2,138.00 | PMC Rider |
