| 2024 | $2,430.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2023 | $10,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2022 | $2,000.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2019 | $1,005.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2018 | $1,425.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2017 | $7,825.00 | Wellesley to Patriot Place (25 mile Sunday) |
| 2013 | $0.00 | PMC Volunteer |
