Player Profile

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.

Playing Record

Senior

Reserve and Youth Team Appearances

Note that appearance data for reserve and youth teams may not be complete. Expand for more information.

Career details

Club	Details
Caledonian Caledonian	(youth)
Mansfield Town Mansfield Town	March 19th, 1982 ; transferred out (rptd June 24th, 1985)
Swindon Town Swindon	July 1st, 1985 (announced June 24th, 1985) (transferred in, fee set by tribunal, total fee £590,000, initial payment of £27,500 initial fee of £27,500, plus 45% of future transfer fee); transferred out (July 22nd, 1993)
Tottenham Hotspur Tottenham	July 22nd, 1993 (transferred in, fee set by tribunal , £1,250,000 ); transferred out (March 24th, 1999)
Aston Villa Aston Villa	March 24th, 1999 (transferred in , £225,000 )
Nottingham Forest Nottingham Forest	March 15th, 2000 ; retired (2000/1)
Notts County Notts County	March 13th, 2001 (loan)
Tottenham Hotspur Tottenham	(appointed reserve team manager)
Northampton Town Northampton Town	October 9th, 2003 (appointed manager); resigned (May 30th, 2006)
Nottingham Forest Nottingham Forest	May 30th, 2006 (appointed manager); sacked (December 26th, 2008)
Newcastle United Newcastle United	rptd January 26th, 2009 (appointed coach)  (appointed assistant manager); resigned (rptd October 18th, 2010)
Hibernian Hibernian	rptd October 18th, 2010 (appointed manager); sacked (rptd November 6th, 2011)
Birmingham City Birmingham	rptd November 24th, 2011 (appointed assistant manager); resigned (rptd June 7th, 2012)
Norwich City Norwich City	rptd June 7th, 2012 (appointed assistant manager); sacked (rptd April 6th, 2014)
Brighton and Hove Albion Brighton	rptd February 3rd, 2015 (appointed assistant manager); resigned (rptd November 12th, 2016)
Aston Villa Aston Villa	rptd November 18th, 2016 (appointed assistant manager); sacked (rptd October 3rd, 2018)
Cambridge United Cambridge United	December 19th, 2018 (appointed manager); sacked (January 29th, 2020)
Northampton Town Northampton Town	rptd October 12th, 2020 (appointed international academy head coach); resigned (rptd October 30th, 2020)
Blackpool Blackpool	rptd October 30th, 2020 (appointed assistant head coach); resigned (rptd June 17th, 2021)
Northampton Town Northampton Town	rptd June 17th, 2021 (appointed assistant manager); resigned (rptd October 30th, 2023)
Southampton Southampton	rptd October 30th, 2023 (appointed coach)