| Tom Lydon | $100.00 |
| Zachary Shepherd | $50.00 |
| 2025 | $150.00 | Wellesley to Wellesley (50 mile Sunday) and Volunteer |
| 2024 | $1,500.00 | Wellesley to Wellesley (50 mile Sunday) and Volunteer |
| 2023 | $2,066.65 | Wellesley to Wellesley (50 mile Sunday) and Volunteer |
| 2022 | $2,810.00 | Wellesley to Wellesley (50 mile Sunday) and Volunteer |
| 2021 | $3,955.00 | Patriot Place to Patriot Place |
| 2020 | $1,126.00 | Wellesley to Wellesley (50 mile Sunday) and Volunteer |
| 2019 | $2,470.00 | Wellesley to Wellesley (50 mile Sunday) and Volunteer |
| 2018 | $0.00 | PMC Volunteer |
| 2017 | $0.00 | PMC Volunteer |
| 2012 | $0.00 | PMC Volunteer |
| 2011 | $0.00 | PMC Volunteer |
| 2010 | $0.00 | PMC Volunteer |
