| 2025 | $2,500.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2024 | $3,554.21 | Wellesley to Wellesley (50 mile Sunday) |
| 2023 | $4,012.00 | Reimagined |
| 2022 | $12,655.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2021 | $10,452.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2020 | $12,531.13 | Wellesley to Wellesley (50 mile Sunday) |
| 2019 | $13,970.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2018 | $10,378.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2017 | $12,610.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2016 | $10,317.88 | Wellesley to Wellesley (50 mile Sunday) |
| 2015 | $10,485.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2014 | $15,101.62 | Wellesley to Wellesley (50 mile Sunday) |
| 2013 | $6,759.00 | Wellesley to Bourne (1-Day, Sat) |
| 2012 | $10,200.00 | Wellesley to Bourne (1-Day, Sat) |
| 2011 | $10,101.00 | Wellesley to Bourne (1-Day, Sat) |
| 2010 | $8,568.00 | Wellesley to Bourne (1-Day, Sat) |
| 2009 | $8,410.00 | Wellesley to Bourne (1-Day, Sat) |
| 2008 | $8,126.00 | Wellesley to Bourne (1-Day, Sat) |
| 2007 | $7,788.00 | Wellesley to Bourne (1-Day, Sat) |
| 2006 | $9,745.00 | Wellesley to Bourne (1-Day, Sat) |
| 2005 | $7,030.00 | Wellesley to Bourne (1-Day, Sat) |
| 2004 | $1,825.00 | Wellesley to Bourne (1-Day, Sat) |
| 2003 | $3,035.00 | Wellesley to Bourne (1-Day, Sat) |
| 2002 | $3,465.00 | Wellesley to Bourne (1-Day, Sat) |
| 2001 | $8,005.00 | Wellesley to Bourne (1-Day, Sat) |
| 2000 | $5,938.00 | Wellesley to Bourne (1-Day, Sat) |
| 1999 | $2,255.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1998 | $1,100.00 | Wellesley to Provincetown Inn (2-Day) |
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