| Kyoko Okamura |
| 2025 | $50.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $8,718.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $10,901.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $7,841.01 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $3,471.00 | Wellesley Century |
| 2020 | $3,886.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,028.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $4,925.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $5,730.00 | Wellesley to Provincetown Monument (2-Day) |
| 2016 | $9,724.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $12,837.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $5,761.89 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $7,677.09 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $6,606.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $6,833.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $7,954.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $10,050.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $3,773.00 | PMC Rider |
| 2007 | $10,465.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2006 | $6,466.00 | Sturbridge to Wellesley (2-Day) |
