| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $50.00 | PMC Fundraiser |
| 2023 | $13,120.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $10,781.66 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $6,923.62 | Wellesley Century |
| 2020 | $4,699.20 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $11,109.39 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $9,344.99 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $13,934.55 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $11,947.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $9,010.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $11,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $10,863.00 | Wellesley to Provincetown Inn (2-Day) |
| 2012 | $6,701.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $7,647.70 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $4,392.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $4,400.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $14,222.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $12,749.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2006 | $9,723.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $10,007.75 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $8,879.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $6,445.00 | Wellesley to Wellesley (2-Day) |
