| Brenda Tynan |
| 2025 | $50.00 | Sturbridge to Provincetown Inn (2-Day) |
| $400.00 | PMC Winter Cycle | |
| 2024 | $51,228.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $82,446.20 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $70,509.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $74,719.00 | Wellesley Century |
| 2020 | $47,662.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $57,976.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $53,991.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $36,371.40 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $8,455.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $10,267.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $8,797.25 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $10,277.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $9,155.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $8,937.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $7,670.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $8,262.00 | Sturbridge to Provincetown Monument (2-Day) |
