| Robert Spear | $150.00 |
| 2025 | $150.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2024 | $0.00 | PMC Volunteer |
| 2023 | $6,000.88 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $6,000.08 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $3,000.00 | Wellesley Century |
| 2020 | $2,082.85 | Bourne to Provincetown Monument (1-Day, Sun) |
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