| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $12,855.00 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $18,900.00 | Wellesley Century |
| 2022 | $10,460.05 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $15,934.05 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $9,473.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $11,581.00 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $7,079.00 | Wellesley to Bourne (1-Day, Sat) |
| 2017 | $7,408.12 | Wellesley to Provincetown Monument (2-Day) |
| 2016 | $135.00 | PMC Rider |
| 2015 | $7,625.70 | Wellesley to Provincetown Monument (2-Day) |
| 2014 | $4,300.00 | Wellesley to Provincetown Monument (2-Day) |
| 2012 | $7,518.00 | Wellesley to Provincetown Monument (2-Day) |
