| SuperBowl Squares | $1,000.00 |
| 2025 | $1,000.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2024 | $5,645.00 | Wellesley to Patriot Place (25 mile Sunday) |
| 2023 | $7,685.00 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $3,065.00 | Patriot Place to Patriot Place |
| 2020 | $2,765.00 | Wellesley to Patriot Place (25 mile Sunday) |
| 2019 | $1,921.00 | Wellesley to Patriot Place (25 mile Sunday) |
