| 2025 | $0.00 | PMC Virtual Rider |
| 2024 | $150.00 | Virtual Ride |
| 2023 | $2,000.94 | Wellesley to Wellesley (50 mile Sunday) |
| 2022 | $100.00 | Virtual Ride |
| 2021 | $100.00 | Virtual Ride |
| 2020 | $125.00 | PMC Rider |
| 2019 | $75.00 | PMC Rider |
| 2018 | $1,635.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2017 | $2,045.00 | Wellesley to Patriot Place (25 mile Sunday) |
| 2016 | $1,665.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2015 | $2,138.54 | Wellesley to Wellesley (50 mile Sunday) |
| 2014 | $2,583.69 | Wellesley to Patriot Place (25 mile Sunday) |
| 2013 | $50.00 | PMC Rider |
| 2012 | $1,635.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2011 | $1,580.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2010 | $1,519.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2009 | $1,000.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2008 | $4,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2007 | $7,691.00 | Wellesley to Bourne (1-Day, Sat) |
| 2006 | $3,782.00 | Wellesley to Bourne (1-Day, Sat) |
