The CWML was started in 1970 as a joint venture of 22 area high schools, Sentry Insurance Company, Wausau Insurance Companies and The University of Wisconsin – Stevens Point. Although the details are sketchy, the idea of was started by Howard Thoyre ( Mathematics Dept UWSP), Charles Johnson ( Chair of Mathematics Dept), John Regnier ( Sentry Insurance), Cal Chamberlain ( Wausau Insurance Companies) and Cal Hessart ( Wausau Insurance Companies) during the Fall of 1970.

The idea was to create an interest in the subject of mathematics for high school students while they are participating in their mathematics courses and to expose them to some of the great careers relating to mathematics, particularly in the insurance field. The first committee of the mathematics to help organize the league appears to have been Howard Thoyre, Richard Schoenecker and Wayne Wild.