1949 - Christopher

1950 - Christopher

1951 - Christopher

1952 - Elkville

1953 - Elkville

1954 - Elkville

1955 - Elkville, Zeigler (Co-Champs)

1956 - Zeigler

1957 - Sesser

1958 - Zeigler

1959 - Christopher

1960 - Elkville

1961 - Elkville, Sesser (Co-Champs)

1962 - Zeigler-Royalton

1963 - Carbondale (University), Christopher (Co-Champs)

1964 - Christopher

1965 - Carbondale (University)

1966 - Sesser-Valier

1967 - Christopher

1968 - Christopher

1969 - Christopher, Sesser-Valier (Co-Champs)

1970 - Christopher

1971 - Christopher

1972 - Carterville

1973 - Carterville

1974 - No Race

1975 - Carterville

1976 - Carterville

1977 - Cartervile

1978 - Carterville

1979 - Christopher

1980 - Christopher, Sesser-Valier (Co-Champs)

1981 - Carterville

1982 - Zeigler-Royalton

1983 - Carterville

1984 - Johnston City, Zeigler-Royalton (Co-Champs)

1985 - Zeigler-Royalon

1986 - Johnston City

1987 - Carterville

1988 - Johnston City

1989 - Carterville

1990 - Christopher-Zeigler-Royalton

1991 - Sesser-Valier

1992 - Johnston City

1993 - Johnston City

1994 - Johnston City

1995 - Carterville, Johnston City (Co-Champs)

1996 - Carterville

1997 - Christopher-Zeigler-Royalton

1998 - Sesser-Valier

1999 - Carterville

2000 - Carterville

2001 - Johnston City

2002 - Carterville

2003 - Carmi-White Co.

2004 - Carterville

2005 - Carmi-White Co.

2006 - Carterville, Johnston City (Co-Champs)

2007 - Carterville

2008 - Carterville

2009 - Sesser-Valier-Waltonville-Woodlawn

2010 - Johnston City

2011 - Carmi-White Co.

2012 - Chester

2013 - Chester, Fairfield (Co-Champs)

2014 - Chester, Johnston City (Co-Champs)

2015 - Eldorado

2016 - Eldorado, Fairfield (Co-Champs)

2017 - Fairfield

2018 - Fairfield

2019 - Fairfield

2020 - (Spring Covid) - Fairfield, Johnston City (Co-Champs)

2021 - Johnston City