| 2025 | $0.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2024 | $3,001.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2023 | $2,800.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2022 | $3,250.00 | Wellesley to Wellesley (50 mile Sunday) and Volunteer |
| 2021 | $3,855.23 | Wellesley to Wellesley (50 mile Sunday) |
| 2020 | $2,524.00 | Wellesley to Patriot Place Teens (25 mile Sun) |
| 2019 | $2,435.00 | Wellesley to Patriot Place Teens (25 mile Sun) |
| 2018 | $2,005.00 | Wellesley to Patriot Place Teens (25 mile Sun) |
| 2017 | $3,212.00 | Wellesley to Patriot Place Teens (25 mile Sun) |
