| 2022 | $9,501.00 | Virtual Ride |
| 2021 | $9,028.06 | Virtual Ride |
| 2020 | $9,895.00 | PMC Rider |
| 2019 | $1,166.00 | Wellesley to Wellesley (50 mile Sunday) and Volunteer |
| 2018 | $5,325.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2016 | $7,546.75 | Wellesley to Bourne + Wellesley Century (2-Day) |
| 2015 | $7,354.85 | Wellesley to Bourne (1-Day, Sat) |
| 2014 | $8,470.86 | Wellesley to Bourne + Wellesley Century (2-Day) |
| 2013 | $9,060.29 | Wellesley to Wellesley (2-Day) |
| 2012 | $7,645.34 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $13,267.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $0.00 | PMC Volunteer |
