| 2024 | $0.00 | PMC |
| $1,500.00 | PMC Unpaved | |
| 2023 | $6,100.00 | Wellesley to Provincetown Monument (2-Day) |
| 2022 | $4,250.00 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $9,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2019 | $100.00 | PMC Fundraiser |
| 2018 | $1,535.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $6,110.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $7,120.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $5,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2014 | $4,395.00 | Wellesley to Bourne (1-Day, Sat) |
| 2013 | $600.00 | PMC Rider |
| 2012 | $550.00 | PMC Rider |
| 2011 | $5,250.00 | Wellesley to Bourne (1-Day, Sat) |
| 2010 | $6,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $6,915.00 | Wellesley to Provincetown Inn (2-Day) |
| 2008 | $7,445.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $7,636.00 | Wellesley to Provincetown Inn (2-Day) |
| 2006 | $100.00 | PMC Fundraiser |
