Swindon narrowly avoided relegation in the 1990–91 season, which Calderwood mostly missed after a tackle by Wolves player Steve Bull caused a serious injury. During the following two seasons, Calderwood returned to be an ever-present in the Swindon side. Now under the management of Glenn Hoddle, Swindon were promoted to the newly founded Premier League at the end of the 1992–93 season after a 4-3 playoff final victory over Leicester. Calderwood was picked for the Football League representative side, playing against their Italian counterparts.