| 2025 | Lombard Orioles | |
| 2024 | Lombard Orioles | |
| 2023 | West Allis Nationals | |
| 2022 | Lombard Orioles | |
| 2021 | Lombard Orioles | |
| 2020 | Lombard Orioles | |
| 2019 | Lombard Orioles | |
| 2018 | Lombard Orioles | |
| 2017 | Lombard Orioles | |
| 2016 | Lombard Orioles | |
| 2015 | Lombard Orioles | |
| 2014 | Lombard Orioles | |
| 2013 | Lombard Orioles | |
| 2012 | Lombard Orioles | |
| 2011 | Lombard Orioles | |
| 2010 | Lombard Orioles | |
| 2009 | Lombard Orioles | |
| 2008 | Lombard Orioles | |
| 2007 | Lombard Orioles | |
| 2006 | Eau Claire Cavaliers | Co-Winner |
| 2006 | Kenosha Kings | Co-Winner |
| 2006 | Lombard Orioles | Co-Winner |
| 2005 | Lombard Orioles | |
| 2004 | Lombard Orioles | |
| 2003 | Chicago Prairie Gravel | |
| 2002 | Lombard Orioles | |
| 2001 | Lombard Orioles | |
| 2000 | Sheboygan A’s | |
| 1999 | Chicago Prairie Gravel | Co-Winner |
| 1999 | Lombard Orioles | Co-Winner |
| 1998 | Green Bay Billys | Co-Winner |
| 1998 | Lombard Orioles | Co-Winner |
| 1997 | Sheboygan A’s | |
| 1996 | Lombard Orioles | |
| 1995 | Green Bay Blue Ribbons | |
| 1994 | Green Bay Blue Ribbons | |
| 1993 | Janesville Aces | Co-Winner |
| 1993 | Lombard Orioles | Co-Winner |
| 1992 | Green Bay Blue Ribbons | Co-Winner |
| 1992 | Lombard Orioles | Co-Winner |
| 1991 | Sheboygan A’s | |
| 1990 | Janesville Aces | |
| 1989 | Janesville Aces | Co-Winner |
| 1989 | Marshfield Chaparrals | Co-Winner |
| 1988 | Oshkosh Giants | |
| 1987 | Madison Avenue Bar | |
| 1986 | Madison Avenue Bar | |
| 1985 | Green Bay Blue Ribbons | |
| 1984 | Delavan | |
| 1983 | Madison Avenue Bar | |
| 1982 | Madison Avenue Bar | |
| 1981 | Green Bay Blue Ribbons | |
| 1980 | Green Bay Blue Ribbons | |
| 1979 | Green Bay Blue Ribbons | Co-Winner |
| 1979 | Horicon Hurricanes | Co-Winner |
| 1978 | Madison Howard Johnson | |
| 1977 | Green Bay Blue Ribbons | |
| 1976 | Green Bay Blue Ribbons | |
| 1975 | Janesville Aces | |
| 1974 | Green Bay Blue Ribbons | |
| 1973 | Green Bay Blue Ribbons | |
| 1972 | Beloit Blues | |
| 1971 | Beloit Blues | |
| 1970 | Green Bay Blue Ribbons |
