| Matthew Kovner | $250.00 |
| 2025 | $250.00 | Wellesley to Provincetown Monument (2-Day) |
| 2024 | $19,328.20 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $14,680.00 | Wellesley to Provincetown Monument (2-Day) |
| 2022 | $14,280.00 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $10,220.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $10,340.55 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $15,948.00 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $11,428.30 | Wellesley to Provincetown Monument (2-Day) |
| 2017 | $10,322.22 | Wellesley to Provincetown Monument (2-Day) |
| 2016 | $9,009.50 | Wellesley to Provincetown Monument (2-Day) |
| 2015 | $8,210.00 | Wellesley to Provincetown Monument (2-Day) |
| 2014 | $6,370.00 | Wellesley to Provincetown Monument (2-Day) |
| 2013 | $6,013.00 | Wellesley to Provincetown Inn (2-Day) |
| 2012 | $6,500.00 | Wellesley to Provincetown Inn (2-Day) |
