| 2024 | $2,125.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2023 | $2,000.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2022 | $0.00 | Virtual Ride |
| 2021 | $3,655.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2020 | $150.00 | PMC Fundraiser |
| 2019 | $1,520.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2018 | $1,405.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2016 | $1,200.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2015 | $1,103.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2014 | $1,117.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2013 | $1,000.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2012 | $1,025.00 | Wellesley to Wellesley (50 mile Sunday) |
