1996 – New Paltz Knights
1997 – Newburgh Cannons
1998 – Wappinger Yankees
1999 – Wappinger Yankees
2000 – Pine Bush Bandits
2001 – Montgomery Cardinals
2002 – Kingston Anaconda Colonials
2003 – Pine Bush Bandits
2004 – NN Cardinals
2005 – Wappinger Yankees
2006 – Wappinger Yankees
2007 – Wappinger Yankees
2008 – Wappinger Yankees
2009 – Wappinger Yankees
2010 – Extra Innings Clippers
2011 – Extra Innings Clippers
2012 – Extra Innings Clippers
2013 – Extra Innings Clippers
2014 – DP Pirates
2015 – DP Pirates
2016 – Newburgh Knights
2017 – Cadets Baseball Academy
2018 – Hudson Valley Athletics
2019 – Hudson Valley Athletics
2020 – Covid Shortened
2021 – Rockland Pirates
2022 – NY Gothams
2023 – Beekman Gamers
2024 – CT Barons
