| 2025 | $0.00 | PMC Virtual Rider |
| 2024 | $2,572.52 | Virtual Ride |
| 2023 | $1,000.00 | Virtual Ride |
| 2022 | $2,820.00 | Virtual Ride |
| 2021 | $3,286.00 | Virtual Ride |
| 2020 | $25.00 | Wellesley to Patriot Place (25 mile Sunday) |
| 2019 | $2,681.00 | Wellesley to Patriot Place (25 mile Sunday) |
| 2015 | $25.00 | PMC Rider |
| 2014 | $150.00 | PMC Rider |
| 2013 | $5,950.67 | Wellesley to Bourne (1-Day, Sat) |
| 2012 | $8,349.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2011 | $6,400.00 | Sturbridge to Provincetown Monument (2-Day) |
