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Anonymous |
| 2025 | $6,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $2,000.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2023 | $2,000.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2022 | $6,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $7,923.53 | Wellesley Century |
| 2020 | $2,981.89 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,134.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $4,900.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $4,800.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $4,548.15 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $7,200.00 | Sturbridge to Provincetown Inn (2-Day) |
