|view Calderwood's match-by-match record|
Lou Macari signed this unknown Scottish centre back from Mansfield in the 1985/1986 pre-season, a Football League tribunal setting the fee at £27,500. It proved to be one of the biggest bargains in the history of the club - by the time Calderwood left eight years later, he was a Swindon legend.
Despite being only 21 years of age, Calderwood was immediately installed as the club captain, and he made his debut on the first day of the season, in a 1-0 away defeat at Wrexham on 17th August 1985. Though that season started badly, it ended fantastically - with the Town breaking the League points record as they streaked to the Fourth Division championship. Calderwood was an ever-present that season, his consistent performances at the heart of the Town's defence winning him the Adver Player of the Year award.
Calderwood was again ever-present the following season, and he led the Town to their second successive promotion, after beating Gillingham in the Play-Off final replay at Selhurst Park.
As Swindon gradually improved in Division Two, the cool, unflappable Calderwood was a rock at the heart of the defence - he missed just thirteen league games over the next three years. At the end of this period, he led the Town to their first promotion to the top flight, after beating Sunderland in the Play-Off Final at Wembley in 1990. The joy was to be short-lived, however, as Swindon were demoted due to the irregular payments scandal, in which Calderwood was implicated - he was arrested just four weeks before the Wembley match, but was released on the same day without charge.
The season after the demotion was disappointing - the Town narrowly avoiding relegation. It was perhaps no coincidence that this season was the one in which Calderwood missed the most games he had in a season - a horror tackle by Wolves legend Steve Bull put him out of the game for five months. He didn't miss another game before the end of his Town career - the following two seasons saw Calderwood as an ever present, and, under Glenn Hoddle, Swindon were promoted at the end of the 1992/1993 season - Calderwood leading the Town to a 4-3 Play-Off final victory over Leicester. He was also picked for the Football League representative side, playing against their Italian counterparts.
Before Calderwood had the chance to lead Swindon into the Premiership, with his contract expired, former manager Ossie Ardiles swooped to take him to Tottenham. Swindon originally refused their derogatory offer of £500,000, but a tribunal set the fee at £1.25 million - then a club record. He went on to become a full international, appearing in the 1998 World Cup for Scotland.
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