The 21-year-old Calderwood was installed as the club captain,[2] and he made his debut on the first day of the season, a 1–0 defeat at Wrexham on 17 August 1985.

Although that season started badly, it ended with the Town breaking the League points record[8] as they won the Fourth Division title.

The following season, Calderwood helped Swindon Town to their achieve their second successive promotion,[2] after beating Gillingham in the playoff final replay at Selhurst Park.

As Swindon gradually improved in Division Two, Calderwood led the defence, missing only 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 playoff final at Wembley in 1990.

[9] 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.

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.

Whilst at Tottenham Hotspur for five years Calderwood played with a succession of defenders including Gary Mabbutt and Ramon Vega.

While at Tottenham he gained many of his Scotland caps, making his debut against Russia in the UEFA Euro 1996 qualifying Group 8 section.

[6] They finally won promotion in 2006 by finishing second in League Two,[6] setting a new club record for clean sheets in a single season, with 25.

[6][14] Calderwood enjoyed an unbeaten league start to his Forest campaign and won the managerial monthly award for August 2006.

[23] Despite this surprise victory, Calderwood suffered criticism after Hibs went on a poor run of results, winning just two of his first fourteen matches as manager.

[27] In June 2011, Birmingham City and Nottingham Forest both approached Hibs with a view to appointing Calderwood as their assistant manager.

[29] Calderwood was appointed assistant manager at Championship club Birmingham City on 24 November 2011, working with Chris Hughton for a third time.

[32] In early February 2015, he was appointed assistant manager at Brighton & Hove Albion, rejoining Hughton for a fourth time.

His new-look squad had a goalless draw at Bradford City on the opening day, before upsetting Championship side Brentford in the League Cup first round in a penalty shootout.

[37] Blackpool head coach Neil Critchley brought Calderwood in to be co-assistant with Mike Garrity in October 2020.