| 2022 | $2,000.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2018 | $0.00 | PMC Rider |
| 2017 | $10,007.90 | Wellesley to Bourne (1-Day, Sat) |
| 2016 | $10,209.01 | Sturbridge to Bourne (1-Day, Sat) |
| 2015 | $14,933.75 | Sturbridge to Bourne (1-Day, Sat) |
| 2013 | $9,073.30 | Wellesley to Bourne (1-Day, Sat) |
| 2012 | $8,499.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $7,768.00 | Sturbridge to Provincetown Inn (2-Day) |
