2020 – Div. 1: Xavier (6-0); Div. 2: Greater New Haven co-op (5-0)
2019 – Div. 1: Fairfield Prep (6-0); Div. 2: Sheehan (6-0)
2018 – Div. 1: Fairfield Prep (6-0); Div. 2: Sheehan (7-0)
2017 – Div. 1: Fairfield Prep (7-0); Div. 2: Hamden (7-0)
2014 – Div. 1: Fairfield Prep (6-0); Div. 2: Lyman Hall (7-0)
2013 – Div. 1: Fairfield Prep (6-0); Div. 2: Lyman Hall (6-1)
2012 – Div. 1: Fairfield Prep (6-0); Div. 2: Lyman Hall (7-0)
2011 – Div. 1: Fairfield Prep (6-0); Div. 2:  Shelton (7-0)
2010 – Fairfield Prep (12-0)
2009 – Fairfield Prep (12-0)
2008 – Group 1 – Fairfield Prep (6-0); Group 2 – North Haven/Foran (4-1)
2007 – Fairfield Prep (12-0)
2006 – Fairfield Prep (6-0)
2005 – Fairfield Prep (13-0)
2004 – Notre Dame (12-0)
2003 – Notre Dame (11-0)
2002 – Cheshire (11-0)
2001 – Cheshire (12-0)
2000 – Cheshire (11-0)
1999 – Cheshire (12-0)
1998 – Cheshire (11-0)
1997 – Cheshire (11-1)
1996 – Cheshire (10-0)
1995 – Cheshire (13-0)