| Joseph Caiazzo | $100.00 |
| 2025 | $100.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $8,296.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $10,615.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $9,855.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $10,260.00 | Wellesley Century |
| 2020 | $6,280.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $8,551.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $8,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $8,050.00 | Wellesley to Wellesley (2-Day) |
| 2016 | $7,500.00 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $9,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $6,901.00 | Wellesley to Provincetown Monument (2-Day) |
| 2013 | $6,700.00 | Wellesley to Bourne (1-Day, Sat) |
