| 2024 | $2,583.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2023 | $2,125.00 | Wellesley to Patriot Place (25 mile Sunday) |
| 2022 | $0.00 | PMC Volunteer |
| 2021 | $50.00 | PMC Volunteer |
| 2020 | $1,035.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $5,021.00 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $4,926.00 | Wellesley to Provincetown Monument (2-Day) |
| 2017 | $4,800.00 | Wellesley to Provincetown Monument (2-Day) |
| 2016 | $4,870.00 | Wellesley to Provincetown Monument (2-Day) |
| 2015 | $5,935.56 | Wellesley to Provincetown Monument (2-Day) |
| 2014 | $170.00 | PMC Volunteer |
| 2013 | $0.00 | PMC Volunteer |
| 2011 | $0.00 | PMC Volunteer |
