Past winners New York Downstate Regional
| Year | # | Event | Venue | Winner |
|---|---|---|---|---|
| 2020 | 0 | NY Downstate Sunfish Regional | Connetquot River DC | Hesse, Dan |
| 2019 | 0 | New York Downstate Regional | Southold YC | Patin, Paul-Jon |
| 2018 | 0 | New York Downstate Regional | Patin, Paul-Jon | |
| 2017 | 0 | New York Downstate Regional | Moriches YC | Patin, Paul-Jon |
| 2014 | 0 | New York Downstate Regional | Westhampton YS | Hesse, Dan |
| 2013 | 0 | New York Downstate Regional | Wet Pants SA | Boger, Bobby |
| 2012 | 0 | New York Downstate Regional | Mattituck Yc | Hesse, Dan |
| 2011 | 0 | New York Downstate Regional | Shattemuc YC | Buruchian, Kevin |
| 2010 | 0 | New York Downstate Regional | Southold YC | Hesse, Dan |
| 2009 | 0 | New York Downstate Regional | Moriches YC | Mockridge, Kenny |
| 2008 | 0 | New York Downstate Regional | Mattituck YC | Hesse, Dan |
| 2007 | 0 | New York Downstate Regional | Sayville YC | Cordero, Eduardo |
| 2006 | 0 | New York Downstate Regional | Mattituck YC | McGinnis, Brian |
| 2005 | 0 | New York Downstate Regional | Cordero, Eduardo | |
| 2004 | 0 | New York Downstate Regional | Cordero, Eduardo | |
| 2003 | 0 | New York Downstate Regional | Moriches YC | Williams, Chris |
| 2002 | 0 | New York Downstate Regional | Southold YC | Mockridge, Kenny |
| 2001 | 0 | New York Downstate Regional | Westhampton YS | Mockridge, Kenny |
| 2000 | 0 | New York Downstate Regional | Wet Pants SA | Greenbaum, Scott |
| 1999 | 0 | New York Downstate Regional | Moriches YC | Mockridge, Kenny |
| 1997 | 0 | New York Downstate Regional | Westhampton YS | Patin, Paul-Jon |
| 1996 | 0 | New York Downstate Regional | Moriches YC | DiResta-Coffill, Christine |
| 1995 | 0 | New York Downstate Regional | Westhampton YS | Patin, Paul-Jon |
| 1994 | 0 | New York Downstate Regional | Southold YC | Abels, Fred |
| 1993 | 0 | New York Regional | Lake Delta YC | Dickinson, Malcolm |
| 1993 | 0 | New York Downstate Regional | Moriches YC | Klingler,Kerry |
| 1992 | 0 | New York Downstate Regional | Westhampton YS | Weeks, Brian |
| 1991 | 0 | New York Downstate Regional | ||
| 1990 | 0 | New York Downstate Regional | Moriches YC | Wefer, Doug |
Design & programming: Gerard -Foxbox- Vos (Sunfish NED458)