| 2025 | $25.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $6,000.50 | Sturbridge to Provincetown Monument (2-Day) |
| 2023 | $6,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $2,050.00 | Patriot Place to Patriot Place |
| $1,000.00 | PMC Winter Cycle | |
| 2020 | $0.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2019 | $1,000.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2018 | $5,150.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $4,500.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2015 | $4,620.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $0.00 | PMC Volunteer |
