| 2024 | $2,476.33 | Wellesley to Wellesley (50 mile Sunday) |
| 2023 | $2,465.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2022 | $1,385.00 | Virtual Ride |
| 2021 | $2,295.00 | Patriot Place to Patriot Place |
| 2020 | $900.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2019 | $2,049.13 | Wellesley to Wellesley (50 mile Sunday) |
| 2018 | $2,295.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2017 | $3,911.69 | Wellesley to Wellesley (50 mile Sunday) |
| 2016 | $4,515.00 | Wellesley to Bourne + Wellesley Century (2-Day) |
| 2015 | $2,410.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2014 | $5,306.64 | Sturbridge to Provincetown Monument (2-Day) |
| 2013 | $2,251.09 | Wellesley to Wellesley (50 mile Sunday) |
| 2012 | $1,245.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2011 | $1,085.00 | Wellesley to Wellesley (50 mile Sunday) |
