| Terry Donovan | $120.00 |
| Kara Wheeler | $200.00 |
|
Chrissy Mcleod |
$25.00 |
| 2025 | $345.00 | Wellesley to Wellesley (50 mile Sunday) and Volunteer |
| $431.00 | PMC Unpaved | |
| $400.00 | PMC Winter Cycle | |
| 2024 | $2,000.00 | Wellesley to Wellesley (50 mile Sunday) |
| $1,900.00 | PMC Unpaved | |
| 2023 | $2,000.00 | Wellesley to Wellesley (50 mile Sunday) |
| $1,600.00 | PMC Unpaved | |
| 2022 | $3,050.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2021 | $2,770.00 | Patriot Place to Patriot Place |
| 2020 | $2,595.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $1,710.00 | Wellesley to Wellesley (50 mile Sunday) |
