2024 –   Div. I: Fairfield Prep (6-0), Div. II – Sheehan (8-1)

2023 – Div. I: Fairfield Prep (6-0), Div. II – Foran (9-0)

2022 – Div I: Fairfield Prep (8-0), Div. II: Foran (7-0)

2021 – Div. I: Fairfield Prep (7-0); Div. II: Amity Regional (8-0)

2020 – Season cancelled due to COVID-19

2019 –  Div. I: Fairfield Prep (8-0); Div. II: Branford (7-1)

2018 – Div. I: Daniel Hand/Fairfield Prep (7-1); Div. II: Shelton (8-0)

2017 – Div. I:  Fairfield Prep (7-0); Div. II: Shelton (7-0)

2016 – Div. I: Fairfield Prep (10-0); Div. II: Notre Dame/Cheshire (11-5); Div. III:  Foran (5-5)

2015 – Div. I: Fairfield Prep, Xavier (9-1); Div. II: North Haven (14-2); Div. III:  Sheehan (5-6)

2015 – Fairfield Prep, Xavier (8-1)

2014 – Fairfield Prep (9-0)

2013 – Fairfield Prep (9-0)

2012 – Fairfield Prep (7-0)

2011 – Fairfield Prep (7-0)

2010 – Cheshire (7-0)

2009 – Fairfield Prep (7-0)

2008 – Fairfield Prep (7-0)

2007 – Fairfield Prep (7-0)

2006 – Hand (7-0)

2005 – Branford (9-0)

2004 – Fairfield Prep (9-0)

2003 – Cheshire (7-0)

2002 – Cheshire (7-0)

2001 – Fairfield Prep (7-0)

2000 – Cheshire (7-0)

1999 – Fairfield Prep (6-0)

1998 – Fairfield Prep (5-0)

1997 – Cheshire (5-0)

1996 – Fairfield Prep (5-0)

1995 – Fairfield Prep, Cheshire, Hand (4-1)