| 2021 | $2,670.00 | Reimagined |
| 2019 | $1,201.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2018 | $0.00 | PMC Volunteer |
| 2017 | $0.00 | PMC Rider |
| 2016 | $1,000.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2015 | $1,445.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2014 | $1,510.00 | Wellesley to Wellesley (50 mile Sunday) |
