2023 - Verona "Cavaliers"

2022 - Verona "Cavaliers"

2021 - Stoughton "Merchants"

2020 - NO CHAMPION
2019 - Verona "Cavaliers"

2018 - Verona "Cavaliers"

2017 - Stoughton "Merchants"

2016 - Albion "Tigers"

2015 - Verona "Cavaliers"
2014 - Ashton
2013 - Middleton "29ers"
2012 - Verona "Cavaliers"
2011 - Cross Plains "Businessmen"
2010 - Verona "Cavaliers"
2009 - Verona "Cavaliers"
2008 - Verona "Cavaliers"
2007 - Monona "Braves"
2006 - Dodgeville "Knights"
2005 - Sun Prairie
2004 - Wiota "Indians"
2003 - Waunakee
2002 - Middleton
2001 - Cottage Grove "Firemen"
2000 - Cottage Grove "Firemen"
1999 - Cazenovia "Reds"
1998 - Cottage Grove "Firemen"
1997 - Cottage Grove "Firemen"
1996 - Cottage Grove "Firemen"
1995 - Wiota "Indians"
1994 - Fort Atkinson "Generals"
1993 - Middleton
1992 - Wiota "Indians"
1991 - Utica "A's"
1990 - Jefferson "Blue Devils"
1989 - Cottage Grove "Firemen"
1988 - Cazenovia "Reds"
1987 - Sun Prairie
1986 - Stoughton "Merchants"
1985 - Waunakee
1984 - Cottage Grove "Firemen"
1983 - Cottage Grove "Firemen"
1982 - Middleton
1981 - Milton
1980 - Milton 
1979 - Middleton
1978 - Cottage Grove "Firemen"
1977 - Cross Plains "Businessmen"
1976 - Middleton

1975 - Middleton

1974 - Black Earth "Bombers"

1973 - Sun Prairie
1972 - Dodgeville "Knights"
1971 - Middleton
1970 - Waunakee
1969 - Waunakee
1968 - Black Earth "Bombers"
1967 - Sun Prairie
1966 - Sauk Prairie "Twins"
1965 - Sun Prairie
1964 - Sun Prairie
1963 - Poynette
1962 - Sun Prairie
1961 - Sun Prairie
1960 - Sun Prairie
1959 - Sun Prairie
1958 - Sun Prairie
1957 - Middleton
1956 - Middleton
1955 - Sauk Prairie "Twins"
1954 - Wyocena
1953 - Wyocena
1952 - Middleton
1951 - Waunakee
1950 - Waunakee
1949 - Waunakee
1948 - NO CHAMPION
1947 - McFarland
1946 - McFarland
1945 - Stoughton "Merchants"
1944 - Cross Plains "Businessmen"
1943 - Cross Plains "Businessmen"
1942 - Madison "Gardner Bakery"
1941 - Madison "3F Laundry"
1940 - Madison "3F Laundry"
1939 - Middleton
1938 - Middleton
1937 - Waunakee
1936 - Ridgeway "Cardinals"
1935 - Madison "Simon Pures"
1934 - Madison "Simon Paints"
1933 - Madison "Simon Paints"
1932 - Lodi
1931 - Sun Prairie
1930 - Sun Prairie
1929 - Middleton