| Year | Varsity | Junior Varsity | Junior High |
| 2023 | Bayport-Blue Point | Southold | Rocky Point |
| 2022 | Bayport-Blue Point & Port Jefferson |
Longwood | West Babylon |
| 2021 | Westhampton Beach | Northport | |
| 2020 | |||
| 2019 | Westhampton Beach | Pierson | Sayville |
| 2018 | Smithtown Christian | Amityville | Riverhead Blue |
| 2017 | Southampton | Harborfields | Southampton |
| 2016 | Bayport-Blue Point & Pierson | Southold | |
| 2015 | Patchogue-Medford | Pierson | East Moriches |
| 2014 | Greenport | Pierson | East Hampton |
| 2013 | Greenport / Shelter Island | Mt. Sinai | |
| 2012 | Greenport / Shelter Island | Greenport / Shelter Island | |
| 2011 | Harborfields | Northport 2 | |
| 2010 | Bayport-Blue Point | Pierson | Rocky Point 8 |
| 2009 | Bayport-Blue Pont | Kings Park | |
| 2008 | Eastport-South Manor | ||
| 2007 | Pierson | Elwood/John Glenn | Elwood |
| 2006 | Elwood/John Glenn | Westhampton Beach | Elwood |
| 2005 | Southold | Riverhead | Babylon |
| 2004 | Bay Shore | Southold | Port Jefferson |
| 2003 | Greenport | Bayport-Blue Point | Mattituck |
| 2002 | Hauppauge | ||
| 2001 | Hauppauge | Rocky Point | Eastport |
| 2000 | Deer Park | ||
| 1999 | Westhampton Beach | Sachem | Riverhead |
| 1998 | Amityville | Stony Brook School | Rocky Point |
| 1997 | Sayville | Mattituck | Miller Place |
| 1996 | Central Islip | Port Jefferson | Wm. Paca |
| 1995 | Longwood | Comsewogue | Saxton |
| 1994 | Sachem | Sachem | Bellport |
| 1993 | Longwood | ||
| 1992 | Bay Shore | ||
| 1991 | Patchogue | ||
| 1990 | Eastport | ||
| 1989 | Brentwood | ||