| Frederic F Parker | $200.00 |
| 2025 | $200.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $6,100.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $6,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $6,025.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $3,459.00 | Wellesley Century |
| 2020 | $4,121.89 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $7,184.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $10,111.10 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $6,247.38 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $5,985.92 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $9,656.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $12,759.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $7,355.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $8,549.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $6,464.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $6,738.09 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $0.00 | PMC Virtual Rider |
| 2008 | $4,215.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $3,771.89 | Sturbridge to Provincetown Inn (2-Day) |
| 2006 | $6,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $3,221.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $3,174.30 | Sturbridge to Bourne (1-Day, Sat) |
