| 2024 | $2,285.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2023 | $2,094.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2022 | $2,062.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2021 | $2,425.23 | Wellesley to Wellesley (50 mile Sunday) |
| 2020 | $1,600.00 | PMC Rider |
| 2019 | $1,605.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2018 | $1,564.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2017 | $1,518.18 | Wellesley to Wellesley (50 mile Sunday) |
| 2016 | $1,225.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2015 | $405.00 | PMC Rider |
| 2014 | $1,000.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2013 | $1,125.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2012 | $1,015.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2011 | $1,400.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2010 | $1,840.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2009 | $1,850.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2008 | $1,645.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2007 | $1,895.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2006 | $2,710.00 | Wellesley to Wellesley (2-Day) |
| 2005 | $2,320.00 | Wellesley to Wellesley (2-Day) |
| 2004 | $2,412.00 | Wellesley to Wellesley (2-Day) |
| 2003 | $2,770.00 | Wellesley to Wellesley (2-Day) |
| 2002 | $2,005.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2001 | $1,810.00 | Wellesley to Provincetown Inn (2-Day) |
| 2000 | $1,500.00 | Wellesley to Provincetown Inn (2-Day) |
| 1999 | $1,300.00 | Wellesley to Bourne (1-Day, Sat) |
