| Donna Canesi | $50.00 |
| 2025 | $50.00 | Reimagined |
| 2024 | $5,246.00 | Reimagined |
| 2023 | $5,987.59 | Reimagined |
| 2022 | $7,734.42 | Wellesley Century and Volunteer |
| 2021 | $9,788.11 | Wellesley Century |
| 2020 | $5,858.45 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $10,076.50 | Wellesley to Provincetown Monument (2-Day) and Volunteer |
| 2018 | $9,646.00 | Sturbridge to Wellesley (2-Day) and Volunteer |
| 2017 | $8,270.00 | Sturbridge to Wellesley (2-Day) and Volunteer |
| 2016 | $7,811.01 | Sturbridge to Wellesley (2-Day) and Volunteer |
| 2015 | $5,762.58 | Sturbridge to Provincetown Inn (2-Day) and Volunteer |
| 2014 | $5,075.00 | Sturbridge to Bourne (1-Day, Sat) and Volunteer |
| 2013 | $0.00 | PMC Volunteer |
| 2012 | $0.00 | PMC Volunteer |
| 2011 | $2,050.00 | PMC Virtual Rider and Volunteer |
| 2010 | $1,000.00 | PMC Volunteer |
| 2009 | $2,888.47 | PMC Virtual Rider and Volunteer |
| 2008 | $0.00 | PMC Volunteer |
| 2006 | $1,000.00 | PMC Virtual Rider and Volunteer |
| 2005 | $0.00 | PMC Volunteer |
| 2004 | $0.00 | PMC Volunteer |
| 2003 | $0.00 | PMC Volunteer |
| 2002 | $0.00 | PMC Volunteer |
| 2001 | $0.00 | PMC Volunteer |
| 2000 | $0.00 | PMC Volunteer |
| 1999 | $0.00 | PMC Volunteer |
| 1998 | $0.00 | PMC Volunteer |
| 1997 | $0.00 | PMC Volunteer |
| 1996 | $0.00 | PMC Volunteer |
