1991 - Carterville

1992 - Elverado, Johnston City, Zeigler-Royalton-Christopher (Tri-Champs)

​1993 - Carterville, Elverado (Co-Champs)

​1994 - Carterville, Elverado, Zeigler-Royalton-Christopher (Tri-Champs)

1995 - Johnston City

1996 - Zeigler-Royalton-Christopher

1997 - Carterville

1998 - Carterville

1999 - Carterville, McLeansboro (Co-Champs)

2000 - Carterville

2001 - Carterville

2002 - Carterville

2003 - Carterville

2004 - Carmi-White Co.

2005 - Carmi-White Co.

2006 - Carmi-White Co., Trico (Co-Champs)

2007 - Eldorado

2008 - Carterville

2009 - Zeigler-Royalton-Christopher

2010 - Carterville

2011 - Trico

2012 - Chester, Johnston City (Co-Champs)

2013 - Chester, Goreville (Co-Champs)

2014 - Chester