Division I
2008 - East Haven (6-1)

2007 - Fairfield Prep (7-0-1)

2006 - Fairfield Prep (7-1)

2005 - Fairfield Prep (5-1-1)
2004 - Fairfield Prep (6-0)
2003 - Notre Dame (7-0)
2002 - West Haven (5-1)
2001 - Fairfield Prep (5-0-1)
2000 - West Haven (4-1-1)
1999 - Fairfield Prep (12-0)
1998 - Hamden (8-1-1)
1997 - Fairfield Prep (9-0-1)
1996 - Notre Dame (9-1)
1995 - Fairfield Prep (5-1)

Division II
2008 - Amity (7-0)

2007 - Amity (5-1)

2006 - Amity (5-1)

2005 - Branford (7-0)
2004 - North Haven (6-1)
2003 - Xavier, North Haven, Branford (4-1)
2002 - Lyman Hall (5-0)
2001 - Lyman Hall (5-0)
2000 - Branford (3-1)
1999 - Cheshire (9-0)
1998 - East Haven (6-0)
1997 - East Haven (6-0)
1996 - East Haven (6-0)
1995 - Lyman Hall, Amity (10-2)