| Rob Sokoloff |
| 2025 | $54.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2024 | $5,088.00 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $4,792.00 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $3,720.00 | Wellesley Century |
| 2021 | $5,000.00 | Wellesley Century |
| 2020 | $400.00 | PMC Fundraiser |
| 2019 | $4,347.10 | Wellesley to Bourne (1-Day, Sat) |
| 2018 | $4,286.00 | Wellesley to Bourne (1-Day, Sat) |
| 2017 | $4,118.00 | Wellesley to Bourne (1-Day, Sat) |
| 2016 | $3,794.00 | Wellesley to Bourne (1-Day, Sat) |
| 2015 | $3,504.00 | Wellesley to Bourne (1-Day, Sat) |
| 2014 | $4,784.89 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $6,540.09 | Wellesley to Provincetown Inn (2-Day) |
| 2012 | $5,706.00 | PMC Rider |
| 2011 | $6,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $6,315.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $5,239.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $8,071.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $3,836.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2006 | $5,244.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $25.00 | PMC Fundraiser |
| 2004 | $7,816.51 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $6,140.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2002 | $5,725.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2001 | $7,284.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2000 | $9,118.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1999 | $7,659.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1998 | $6,538.00 | Wellesley to Provincetown Inn (2-Day) |
