| 2025 | $0.00 | PMC Virtual Rider |
| 2024 | $2,000.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2023 | $2,604.40 | Wellesley to Wellesley (50 mile Sunday) |
| 2022 | $3,000.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2021 | $4,195.97 | Wellesley Century |
| 2020 | $1,325.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2019 | $2,219.02 | Wellesley to Wellesley (50 mile Sunday) |
| 2018 | $4,945.36 | Wellesley to Provincetown Inn (2-Day) |
| $250.00 | PMC Winter Cycle | |
| 2017 | $4,836.00 | Wellesley to Provincetown Inn (2-Day) |
| $250.00 | The Resolution by PMC | |
| 2016 | $4,500.00 | Wellesley to Provincetown Inn (2-Day) |
| $675.00 | The Resolution by PMC | |
| 2015 | $4,572.00 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $1,348.62 | Wellesley to Wellesley (50 mile Sunday) |
