| 2025 | $0.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $7,678.75 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $6,002.00 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $7,785.00 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $7,322.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2020 | $9,093.00 | Wellesley to Bourne (1-Day, Sat) |
| 2019 | $8,600.00 | Wellesley to Bourne (1-Day, Sat) |
| 2018 | $9,012.00 | Wellesley to Bourne (1-Day, Sat) |
| 2017 | $4,245.00 | Wellesley to Bourne (1-Day, Sat) |
| 2016 | $7,760.56 | Wellesley to Bourne (1-Day, Sat) |
| 2015 | $7,375.25 | Wellesley to Bourne (1-Day, Sat) |
| 2014 | $7,103.00 | Wellesley to Bourne (1-Day, Sat) |
| 2013 | $8,750.00 | Wellesley to Provincetown Inn (2-Day) |
| 2012 | $6,650.00 | Wellesley to Provincetown Inn (2-Day) |
| 2011 | $6,450.00 | Wellesley to Provincetown Inn (2-Day) |
| 2010 | $5,230.00 | Wellesley to Provincetown Inn (2-Day) |
| 2009 | $6,296.81 | Wellesley to Provincetown Inn (2-Day) |
| 2008 | $4,363.32 | Wellesley to Provincetown Inn (2-Day) |
| 2007 | $3,731.67 | Wellesley to Provincetown Inn (2-Day) |
| 2006 | $3,300.00 | Wellesley to Provincetown Inn (2-Day) |
| 2005 | $3,575.00 | Wellesley to Provincetown Inn (2-Day) |
| 2004 | $3,070.00 | Wellesley to Bourne (1-Day, Sat) |
| 2003 | $2,640.00 | Wellesley to Provincetown Inn (2-Day) |
| 2002 | $2,725.00 | Wellesley to Provincetown Inn (2-Day) |
| 2001 | $2,165.00 | Wellesley to Provincetown Inn (2-Day) |
| 2000 | $1,475.00 | Wellesley to Bourne (1-Day, Sat) |
| 1999 | $870.00 | Wellesley to Bourne (1-Day, Sat) |
| 1997 | $2,285.00 | PMC Rider |
