| Alison Angel | $137.00 |
| Melissa Anderson | $100.00 |
|
Eilean Kozak |
| 2025 | $287.00 | PMC Virtual Rider |
| 2024 | $5,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $4,000.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2022 | $5,000.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2021 | $5,000.00 | Wellesley Century |
| 2020 | $1,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $4,925.00 | Sturbridge to Provincetown Inn (2-Day) |
