| 2025 | $0.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $10,597.75 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $13,125.10 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $11,400.95 | Wellesley to Bourne (1-Day, Sat) |
| $25.00 | PMC Unpaved | |
| 2021 | $9,120.00 | Wellesley Century |
| 2020 | $9,140.00 | Wellesley to Bourne (1-Day, Sat) |
| 2019 | $9,225.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $8,848.86 | Wellesley to Bourne (1-Day, Sat) |
| 2017 | $9,326.41 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $9,848.04 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $9,571.00 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $7,871.12 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $6,949.00 | Wellesley to Provincetown Inn (2-Day) |
| 2012 | $6,711.00 | Wellesley to Provincetown Inn (2-Day) |
| 2011 | $5,984.50 | Wellesley to Provincetown Inn (2-Day) |
| 2010 | $6,834.00 | Wellesley to Provincetown Inn (2-Day) |
| 2009 | $8,395.00 | Wellesley to Provincetown Inn (2-Day) |
| 2008 | $6,833.34 | Wellesley to Provincetown Inn (2-Day) |
| 2007 | $4,545.00 | Wellesley to Wellesley (2-Day) |
| 2006 | $3,875.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $7,775.00 | Wellesley to Provincetown Monument (2-Day) |
| 2004 | $5,775.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $4,750.00 | Wellesley to Provincetown Inn (2-Day) |
| 2002 | $5,405.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2001 | $2,428.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2000 | $3,230.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1999 | $2,260.00 | Wellesley to Bourne (1-Day, Sat) |
