| 2024 | $2,772.10 | Wellesley to Wellesley (50 mile Sunday) |
| 2018 | $1,875.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2017 | $1,200.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2016 | $1,050.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2015 | $1,400.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2013 | $1,890.00 | Wellesley to Wellesley (50 mile Sunday) |
