| William Grimes | $250.00 |
| 2025 | $250.00 | PMC Virtual Rider |
| 2024 | $4,220.00 | Virtual Ride |
| 2023 | $4,173.00 | Virtual Ride |
| 2022 | $4,038.00 | Virtual Ride |
| 2021 | $4,065.00 | Virtual Ride |
| 2020 | $7,008.00 | Wellesley to Bourne (1-Day, Sat) |
| $0.00 | PMC Winter Cycle | |
| 2019 | $7,175.00 | PMC Rider |
| 2018 | $8,315.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $6,305.00 | PMC Rider |
| 2016 | $6,048.37 | Wellesley to Bourne (1-Day, Sat) |
| 2015 | $4,775.00 | PMC Rider |
| 2014 | $7,771.07 | Wellesley to Provincetown Monument (2-Day) |
| 2013 | $8,656.09 | Wellesley to Provincetown Inn (2-Day) |
| 2012 | $9,025.00 | Wellesley to Provincetown Monument (2-Day) |
| 2011 | $11,047.00 | Wellesley to Provincetown Inn (2-Day) |
| 2010 | $7,370.00 | Wellesley to Provincetown Inn (2-Day) |
| 2009 | $11,615.00 | Wellesley to Provincetown Inn (2-Day) |
| 2007 | $200.00 | PMC Fundraiser |
| 2006 | $50.00 | PMC Fundraiser |
| 2005 | $5,760.00 | Wellesley to Provincetown Monument (2-Day) |
| 2004 | $4,130.00 | Wellesley to Bourne (1-Day, Sat) and Volunteer |
| 2003 | $6,104.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2002 | $5,675.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2001 | $9,346.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2000 | $4,687.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1999 | $1,875.00 | Wellesley to Provincetown Inn (2-Day) |
