| 2024 | $1,763.00 | Virtual Ride |
| 2023 | $1,340.00 | Virtual Ride |
| 2022 | $560.00 | Virtual Ride |
| 2021 | $2,230.00 | Patriot Place to Patriot Place |
| 2020 | $1,535.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2019 | $1,025.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2018 | $1,551.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2017 | $1,200.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2016 | $3,700.00 | Wellesley to Bourne (1-Day, Sat) |
| 2015 | $3,400.45 | Wellesley to Bourne (1-Day, Sat) |
