| 2023 | $50.00 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $50.00 | PMC Fundraiser |
| 2021 | $4,240.00 | Wellesley Century |
| 2020 | $305.00 | Wellesley to Wellesley (2-Day) |
| 2019 | $7,076.00 | Sturbridge to Wellesley (2-Day) |
| 2018 | $5,636.39 | Wellesley to Wellesley (2-Day) |
| 2017 | $5,501.20 | Wellesley to Wellesley (2-Day) |
| 2016 | $5,528.58 | Wellesley to Wellesley (2-Day) |
| 2015 | $5,600.78 | Wellesley to Wellesley (2-Day) |
| 2014 | $6,905.16 | Wellesley to Wellesley (2-Day) |
| 2013 | $5,000.83 | Wellesley to Wellesley (2-Day) |
| 2012 | $3,868.10 | Wellesley to Bourne (1-Day, Sat) |
