| Jeffrey Gillis | $100.00 |
| 2025 | $4,100.00 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $4,050.00 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $4,250.00 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $5,100.00 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $9,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2019 | $4,205.00 | Wellesley to Bourne (1-Day, Sat) |
| 2017 | $6,600.00 | Wellesley to Bourne (1-Day, Sat) |
| 2016 | $4,875.00 | Wellesley to Bourne (1-Day, Sat) |
| 2015 | $4,400.00 | Wellesley to Bourne (1-Day, Sat) |
| 2014 | $4,250.00 | Wellesley to Bourne (1-Day, Sat) |
| 2013 | $4,050.00 | Wellesley to Bourne (1-Day, Sat) |
| 2011 | $3,465.00 | Wellesley to Bourne (1-Day, Sat) |
| 2010 | $5,316.25 | Wellesley to Bourne (1-Day, Sat) |
| 2008 | $6,700.00 | Wellesley to Bourne (1-Day, Sat) |
