On May 14, 1986, Calhoun was named the head coach at the University of Connecticut. After completing his first season just 9–19, Calhoun led the Huskies to a 20–14 record in 1988 and a bid to National Invitation Tournament, where they defeated Ohio State to win the NIT championship. In 1990, Calhoun was named the consensus National Coach of the Year after leading the Huskies to their first Big East championship, the NCAA Tournament Elite Eight, and a 29–6 record in only his fourth year at the helm.