| Rob Sokoloff |
| 2025 | $54.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2024 | $4,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $3,724.00 | Wellesley Century |
| 2021 | $100.00 | Virtual Ride |
| 2020 | $0.00 | PMC Rider |
| 2019 | $4,776.84 | Wellesley to Bourne (1-Day, Sat) |
| 2018 | $4,416.09 | Wellesley to Bourne (1-Day, Sat) |
| 2016 | $4,116.62 | Wellesley to Bourne (1-Day, Sat) |
| 2015 | $3,700.00 | Wellesley to Bourne (1-Day, Sat) |
| 2010 | $0.00 | PMC Volunteer |
