| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $6,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2023 | $3,050.00 | Wellesley Century |
| 2022 | $4,314.06 | Wellesley Century |
| 2021 | $3,050.00 | Wellesley Century |
| 2020 | $1,260.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $5,560.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $2,200.00 | Wellesley to Wellesley (50 mile Sunday) |
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