Bennett began his collegiate coaching career at the University of Wisconsin-Stevens Point, where he won 173 games. He was named NAIA Coach of the Year after leading the Pointers to a 28-4 record and national runner-up finish in 1984. In 1985, Bennett moved to the University of Wisconsin-Green Bay. Bennett took the Phoenix to the second round of the NIT tournament in 1990 and led the team to its first NCAA tournament berth in 1991. In 1995, Bennett was named the head men’s basketball coach at the University of Wisconsin-Madison. During his tenure at Wisconsin he compiled a record of 94-68. He led the Badgers to the Final Four in 2000. In all, he took Wisconsin to three NCAA tournament appearances and earned one NIT bid. Bennett was the first Wisconsin coach to win 20 games in a season. He retired from the University of Wisconsin in November 2000.