1996: Green Bay Corona
1997: Fond du Lac FC
1998: Sheboygan SC
1999: Barcelona
2000: Menasha Hacienda
2001: Sheboygan Atlas
2002: Green Bay Providencia
2003: Manitowoc Maritime SC
2004: Neenah Deportivo Cañada
2005: Menasha Toluca
2006: Manitowoc Maritime SC
2007: Washington St. Kickers
2008: Team Miller Lites
2009: F.C. Dynamite
2010: Maritime Bay SC
2011: Fond du Lac CF
2012: D.C. Express
2013: Team Green Bay Packaging
2014: FC Oshkosh
2015: Westchester United
2016: FC Oshkosh
2017: FC Oshkosh
2018: Millerlitecup
2019: Millerlitecup
2020: No competition due to COVID-19 pandemic
2021: Millerlitecup
2022: No competition
2023: Wolves FC