A hard-working defender, who always gave his best for Tottenham, Colin Calderwood provided the backbone of the Spurs defence through the Ardiles and Francis eras.

The Scots defender tried to make his start in football at West Ham United, but was knocked back, so went down the leagues to begin at Mansfield Town, where he made over 100 appearances.  He was snapped up by Swindon Town and was there during Ossie Ardiles' management, when they were promoted, but then demoted because of financial irregularities, before he finally helped them to promotion, with Glenn Hoddle in charge, to the Premier League in 1993 via a play-off final against Leicester City.  Calderwood was team captain at the County Ground and played in successful play-off finals in 1986 (Division Four), 1987 (Division Three), 1990 (Division Two) and 1993 (Division One).

He joined Tottenham that summer for £1,250,000, as Ardiles sought to bolster the defence with his former captain, despite Calderwood having no top flight experience.  A solid defender, who could tackle and was good in the air, but lacked the pace and distribution skills to be a top class centre half, Calderwood gave Spurs a tough presence in the middle of the back four they had been missing for some time and showed that Ardiles' judgement had been sound.  Never regarded as a top Tottenham players by many fans, Calderwood always gave a good deal of effort and passion.  Good in the air, his ability on the ball was his great strength and could pick long passes out of defence to hit his front men.

Colin settled in well and when he was ousted form the side by new signing Kevin Scott in 1993-94, the Scot battled back to regain his place alongside Sol Campbell in the middle of defence.

While at Spurs, he became a regular in the Scotland side, making his debut at 30 and going to Euro 1996 and the World Cup of 1998 with his country.

After leaving Tottenham, Calderwood moved on to Aston Villa, but injuries had taken their toll and he lacked the consistency of his former years and played a handful of games there and at Nottingham Forest where he left Villa Park for.  His last stop in his playing career was a loan spell at Notts. County.

Having taken a keen interest in coaching and obtained his badges, Colin went on to manage Tottenham's reserve side before he stepped into League management with Northampton Town in (9th October 2003) getting them automatically promoted as runners-up in League Two (with a record number of clean sheets = 25) and Nottingham Forest (May 2006), where he took them to the 2007 promotion play-offs, where they lost out to Yeovil Town.  However, despite a rocky season with some fans turning against him in 2007-08, he lead the side to automatic promotion from League One.  Unfortunately, things did not go so well in the Championship and four wins out of 25 games saw his contract terminated on Boxing Day 2008.

In February 2009, he was back in work and in a Tottenham setting, although it was at Newcastle United, where he became a coach under Chris Hughton and Joe Kinnear at St. James' Park.  With Alan Shearer taking over as manager for the last eight games of the season, he could not stop the Magpies getting relegated to the Championship and the end of the season brought rumours of Calderwood being linked with the manager's jobs at Chesterfield, QPR, Aberdeen and Watford.

Colin continued alongside Hughton for the 2009-10 season and they took the club to the Championship title and back into the Premier League.  A third of the way through the 2010-11 season, Calderwood applied for the job as manager at Hibernian, as he wanted to get back into the manager's office himself and despite a tough start at the struggling club, he managed to turn things around and move the club away from the bottom of the table.  However, a lack of consistency in the club's results and a big derby hammering by Hearts brought the sack for Colin and he teamed up again with Chris Hughton as his assistant at Birmingham City, taking them to the play-offs and then following his former Spurs team-mate to Norwich City in the summer of 2012.  Followed Hughton to Brighton & Hove Albion when he took over at the Amex, but left his former team-mate to take on the post of assistant manager at Aston Villa in November 2016.