| Paul and Elaine |
| 2025 | $6,295.00 | Wellesley to Patriot Place (25 mile Sunday) |
| 2024 | $7,660.65 | Wellesley to Wellesley (50 mile Sunday) |
| 2023 | $7,100.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2022 | $6,970.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2021 | $8,470.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2020 | $4,582.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2019 | $7,580.00 | Wellesley to Wellesley (50 mile Sunday) |
| 1993 | $1,310.00 | PMC Rider |
