| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $10,011.17 | Wellesley to Bourne (1-Day, Sat) and Volunteer |
| 2023 | $4,895.65 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $3,868.26 | Virtual Ride |
| 2021 | $5,640.00 | Wellesley Century and Volunteer |
| 2020 | $8,416.00 | Wellesley to Bourne (1-Day, Sat) |
| 2019 | $7,382.50 | Bourne to Provincetown Inn (1-Day, Sun) and Volunteer |
| 2018 | $4,537.50 | Wellesley to Wellesley (50 mile Sunday) |
| 2017 | $6,040.56 | Bourne to Provincetown Monument (1-Day, Sun) |
| 2016 | $4,641.12 | Bourne to Provincetown Monument (1-Day, Sun) |
| 2015 | $1,450.00 | Wellesley to Wellesley (50 mile Sunday) |
