| Year | # | Event | Venue | Winner |
|---|---|---|---|---|
| 2019 | 0 | Great Pumpkin Regatta | Johnson Slough YC | Chapman, Rich |
| 2018 | 0 | Great Pumpkin Regatta | Johnson Slough YC | Kastel, Mark |
| 2017 | 0 | Great Pumpkin Regatta | Johnson Slough YC | Chapman, Rich |
| 2016 | 0 | Great Pumpkin Regatta | Johnson Slough YC | Chapman, Rich |
| 2015 | 0 | Great Pumpkin Regatta | Johnson Slough YC | Findlay, Bob |
| 2014 | 0 | Great Pumpkin Regatta | Johnson Slough YC | Chapman, Rich |
| 2013 | 0 | Great Pumpkin Regatta | Johnson Slough YC | Chapman, Rich |
| 2012 | 0 | Great Pumpkin Regatta | Johnson Slough YC | Chapman, Rich |
| 2011 | 0 | Great Pumpkin Regatta | Johnson Slough YC | |
| 2010 | 0 | Great Pumpkin Regatta | Johnson Slough YC | Findlay, Bob |
| 2009 | 0 | Great Pumpkin Regatta | Johnson Slough YC | Findlay, Bob |
| 2008 | 0 | Great Pumpkin Regatta | Johnson Slough YC | Chapman, Rich |
| 2007 | 0 | Great Pumpkin Regatta | Johnson Slough YC | Schappe, Scott |
| 2006 | 0 | Great Pumpkin Regatta | Johnson Slough YC | Cancelled |
| 2005 | 0 | Great Pumpkin Regatta | Johnson Slough YC | |
| 2004 | 0 | Great Pumpkin Regatta | Johnson Slough YC | Chapman, Rich |
| 2003 | 0 | Great Pumpkin Regatta | Johnson Slough YC | Nelson, Bill |
| 2002 | 0 | Great Pumpkin Regatta | Johnson Slough YC | Hanselman, Fritz |
| 2001 | 0 | Great Pumpkin Regatta | Johnson Slough YC | Feldman, Dan |
| 2000 | 0 | Great Pumpkin Regatta | Johnson Slough YC | |
| 1999 | 0 | Great Pumpkin Regatta | Johnson Slough YC | Feldman, Dan |
| 1998 | 0 | Great Pumpkin Regatta | Johnson Slough YC | Chapman, Rich |
| 1997 | 0 | Great Pumpkin Regatta | Johnson Slough YC | Findlay, Bob |
| 1996 | 0 | Great Pumpkin Regatta | Johnson Slough YC | Liebl, James |
| 1995 | 0 | Great Pumpkin Regatta | Johnson Slough YC | |
| 1994 | 0 | Great Pumpkin Regatta | Johnson Slough YC | Liebl, James |
| 1993 | 0 | Great Pumpkin Regatta | Johnson Slough YC | Findlay, Bob |
| 1992 | 0 | Great Pumpkin Regatta | Johnson Slough YC | Findlay, Bob |
| 1991 | 0 | Great Pumpkin Regatta | Johnson Slough YC | |
| 1990 | 0 | Great Pumpkin Regatta | Johnson Slough YC | Findlay, Bob |
| 1989 | 0 | Great Pumpkin Regatta | Johnson Slough YC | Findlay, Bob |
| 1988 | 0 | Great Pumpkin Regatta | Johnson Slough YC | Vickers, Bill |