The WIAA goes back to 1913 to determine its first boys cross country tournament champion. Milwaukee Riverside was the first team champion.
There was one class of competition until 1933, when for one year it changed to two divisions. The format reverted back in 1934 because of insufficient school participation until 1949 when it returned to two classes. It became three classes in 1956 and has remained at three except in 1968, 1969 and 1970 when it was two classes. Terminology was changed to Divisions 1-2-3 instead of Classes A-B-C in 1990. Milwaukee Riverside not only won the first championship, but also the next seven, as well as six more from 1923 to 1928. Riverside has won the most championships with 16, and all of them were won between 1913 and 1936. South Milwaukee is next with 10 titles; Stevens Point has won nine titles; Shorewood has won eight and Fennimore seven; Albany, Madison West and Milwaukee Bay View have six; and Cochrane-Fountain City, Milwaukee Washington, Port Washington and Whitefish Bay have five. Milwaukee Washington also has been runner-up 11 times. Only four boys have won three individual championships. They are Jim Brice of Wrightstown (1975-77), Paul Voss of Clinton (1977-79), Phil Downs of Madison Memorial (1989-91) and Chris Solinsky of Stevens Point (2000-02). There have been 30 boys in Wisconsin who have won two individual titles. Milwaukee Riverside has produced the most individual champions with 10, followed by South Milwaukee with eight. Stevens Point has produced six champions, and Menomonee Falls North has produced five. Boscobel, Madison Memorial, Milwaukee South and McFarland have claimed four individual championships. Individual titles have been won by runners from 104 different schools.