| 2024 | $11,034.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $150.00 | PMC Fundraiser |
| 2021 | $252.00 | PMC Fundraiser |
| 2020 | $5,160.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $125.00 | PMC Rider |
| 2018 | $8,125.00 | Wellesley to Provincetown Monument (2-Day) |
| 2017 | $9,014.00 | Wellesley to Provincetown Monument (2-Day) |
| 2016 | $6,096.00 | Wellesley to Provincetown Monument (2-Day) |
| 2015 | $5,011.00 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $236.00 | PMC Rider |
| 2013 | $4,036.00 | Wellesley to Wellesley (2-Day) |
| 2012 | $0.00 | PMC |
| 2011 | $3,938.00 | Wellesley to Wellesley (2-Day) |
| 2010 | $4,540.00 | Wellesley to Wellesley (2-Day) |
