| Kenneth Tubman | |
| Ken Sokol |
| 2025 | $25.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $12,731.30 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $12,322.15 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $10,427.10 | Sturbridge to Provincetown Inn (2-Day) |
| $100.00 | PMC Unpaved | |
| 2021 | $978.55 | PMC Rider |
| 2020 | $2,526.53 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $7,722.90 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $6,770.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $7,816.87 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $7,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $7,523.87 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $7,258.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $9,587.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $4,635.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $5,978.00 | Sturbridge to Provincetown Inn (2-Day) |
