Beginning his career at Wimbledon, Wise came to prominence as a member of the "Crazy Gang", and in 1988, was part of the team that won the FA Cup in an upset victory over Liverpool. In 1990, he joined Chelsea, becoming captain three years later under the stewardship of Glenn Hoddle. During his time at Stamford Bridge, Wise won two FA Cups, a League Cup and a UEFA Cup Winners' Cup, and is the club's second most successful captain, behind John Terry. Wise was a popular figure amongst the Chelsea support, and was named the club's Player of the Year on two occasions. In June 2001, he was sold to Leicester City.