| 2023 | $0.00 | Virtual Ride |
| 2022 | $0.00 | Virtual Ride |
| 2021 | $50.00 | Virtual Ride |
| 2020 | $50.00 | PMC Rider |
| 2019 | $50.00 | PMC Rider |
| 2018 | $1,250.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2017 | $1,200.00 | Wellesley to Patriot Place (25 mile Sunday) |
| 2016 | $1,100.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2015 | $1,000.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2014 | $1,000.00 | Wellesley to Patriot Place (25 mile Sunday) |
| 2012 | $1,150.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2011 | $695.00 | Wellesley to Wellesley Teens (50 mile Sunday) |
| 2010 | $519.00 | Wellesley to Wellesley Teens (50 mile Sunday) |
| 2009 | $525.00 | Wellesley to Wellesley Teens (50 mile Sunday) |
| 2008 | $0.00 | PMC Volunteer |
