| 2025 | $0.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2024 | $2,418.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2023 | $2,465.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2022 | $2,625.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2021 | $2,640.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2020 | $0.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2019 | $2,030.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2018 | $1,200.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2017 | $0.00 | PMC Volunteer |
| 2016 | $0.00 | PMC Volunteer |
| 2015 | $0.00 | PMC Volunteer |
| 2014 | $0.00 | PMC Volunteer |
