1955-56 - Sesser

1956-57 - Chistopher, Sesser (Co-Champs)

1957-58 - Sesser, Zeigler, Carterville, Christopher (Quad-Champs)

1958-59 - Zeigler

1959-60 - Elkville

1960-61 - Elkville

1961-62 - Elkville

1962-63 - Elverado, Zeigler-Royalton (Co-Champs)

1963-64 - Elverado, Sesser-Valier, Zeigler-Royalton (Tri-Champs)

1964-65 - Zeigler-Royalton

1965-66 - Carbondale (University)

1966-67 - Carbondale (University)

1967-68 - Carterville

1968-69 - Trico

1969-70 - Trico

1970-71 - Trico

1971-72 - Zeigler-Royalton

1972-73 - Carterville, Christopher (Co-Champs)

1973-74 - Christopher, Zeigler-Royalton (Co-Champs)

1974-75 - No Race

1975-76 - No Race

1976-77 - Johnston City

1977-78 - Johnston City

1978-79 - Zeigler-Royalton

1979-80 - Zeigler-Royalton

1980-81 - Sesser-Valier

1981-82 - Zeigler-Royalton

1982-83 - Carterville, Zeigler-Royalton (Co-Champs)

1983-84 - Carterville

1984-85 - Johnston City

1985-86 - Sesser-Valier

1986-87 - Cartervile

1987-88 - Carterville

1988-89 - Christopher, Sesser-Valier (Co-Champs)

1989-90 - Christopher, Sesser-Valier (Co-Champs)

1990-91 - Sesser-Valier

1991-92 - Sesser-Valier

1992-93 - Carterville, Johnston City, Sesser-Valier (Tri-Champs)

1993-94 - Sesser-Valier

1994-95 - Carterville, Sesser-Valier (Co-Champs)

1995-96 - Carterville

1996-97 - Sesser-Valier

1997-98 - Christopher, Johnston City (Co-Champs)

1998-99 - Johnston City

1999-00 - Johnston City

2000-01 - Sesser-Valier

2001-02 - Johnston City

2002-03 - Carterville