| 2025 | $1,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $70,358.75 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $67,849.75 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $42,826.26 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $56,442.00 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $38,225.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $53,917.06 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $40,283.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $54,970.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $85,280.00 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $79,788.33 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $84,117.33 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $54,979.33 | Wellesley to Provincetown Inn (2-Day) |
| 2012 | $87,521.00 | Wellesley to Provincetown Inn (2-Day) |
| 2011 | $62,507.33 | Wellesley to Provincetown Inn (2-Day) |
| 2010 | $58,158.99 | Wellesley to Provincetown Inn (2-Day) |
| 2009 | $95,052.67 | Wellesley to Provincetown Inn (2-Day) |
| 2008 | $85,466.66 | Wellesley to Provincetown Inn (2-Day) |
| 2007 | $92,713.14 | Wellesley to Provincetown Inn (2-Day) |
| 2006 | $88,252.25 | Wellesley to Provincetown Inn (2-Day) |
| 2005 | $130,758.70 | Wellesley to Provincetown Inn (2-Day) |
| 2004 | $130,877.00 | Wellesley to Provincetown Inn (2-Day) |
| 2003 | $120,516.00 | Wellesley to Provincetown Inn (2-Day) |
| 2002 | $93,064.00 | Wellesley to Provincetown Inn (2-Day) |
| 2001 | $103,656.00 | Wellesley to Provincetown Inn (2-Day) and Volunteer |
| 2000 | $109,117.00 | Wellesley to Provincetown Inn (2-Day) |
| 1999 | $65,097.34 | Wellesley to Provincetown Inn (2-Day) |
| 1998 | $38,060.00 | Wellesley to Provincetown Inn (2-Day) |
| 1997 | $32,294.95 | PMC Rider |
| 1996 | $15,517.00 | PMC Rider |
| 1995 | $9,854.00 | PMC Rider |
| 1994 | $15,000.00 | PMC Rider |
| 1993 | $8,383.20 | PMC Rider |
| 1992 | $9,631.52 | PMC Rider |
| 1991 | $6,643.80 | PMC Rider |
| 1990 | $5,000.00 | PMC Rider |
