Managerial Career
His first two spells in management (between January 1989 and June 1990), first with Portsmouth and then with Plymouth Argyle, lasted just a few months each. Shortly afterwards, he linked up as a non-contract player with his former England team-mate Phil Neal, who was then manager at Bolton Wanderers.
He later worked under Brian Little on the coaching staff at Leicester City (1991–1994) and Aston Villa (1994–96) before moving back into management with Wycombe Wanderers in September 1996. Wycombe were bottom of Division Two when Gregory took over, but he oversaw a massive improvement in league form which saw the club climb up to a secure mid-table finish. However, the side he put together failed to progress any further, and they also suffered an embarrassing FA Cup exit to Basingstoke Town. Wycombe were performing well in February 1998 when Gregory quit to take the manager's job back at Aston Villa. He helped improve Villa's league form during the final 3 months of the 1997-98 season and they qualified for the UEFA Cup.
Halfway through the 1998-99 season. Villa were Premiership leaders but a slump in form saw the club eventually finish sixth in the final table and miss out on a first premership title Villa reached the FA Cup final in 2000 but lost to Chelsea. Gregory finally quit in January 2002, with Villa going on to finish eighth that season. Gregory's spell at Villa is also notable as he became the last manager to field an all English starting 11 in the Premiership, until Steve McClaren's Middlesbrough did the same against Fulham on 7 May 2006.
Gregory's next spell in management was with Derby County (January 2002 - March 2003). When he took charge at Derby they were bottom of the Premiership, but after winning both of his first two games at the helm it looked as though he might be able to save them from relegation. Unfortunately, seven defeats from their final eight fixtures saw Derby slip out of the Premiership after six years. The club's financial problems meant that Gregory hadn't purchased any players during the 2002-03 season, and their subsequent form in Division One was disappointing.
He was sacked in March 2003 for alleged misconduct but later won £1 million in compensation for unfair dismissal. Due to the ongoing lawsuit, Gregory was unable to apply for another managerial position for some time, so he spent most of the next three years working as a television pundit.
On 20 September 2006 he was unveiled as manager of Queens Park Rangers. He replaced Gary Waddock, who had stepped down following a poor succession of results that had left the club bottom of the Football League Championship. This appointment caused a schism among QPR fans, some of whom saw Gregory's friendship with controversial chairman Gianni Paladini as a conflict of interest. After a decent start with successive victories over Hull City and Southampton, Rangers form dipped before winning three on the bounce (including a victory at (then) league leaders Cardiff City). Unfortunately, results did not continue to improve, and relegation looked a distinct possibility for Gregory's men. However, following a fine late season run, QPR beat Cardiff 1–0 at Loftus Road on 21 April 2007 to secure their Championship status for another year. Gregory was sacked as QPR manager on 1 October 2007, after another string of poor performances.
On 8 December 2009, Gregory was appointed the manager of Israeli club Maccabi Ahi Nazareth. He led them to relegation.
On 18 May 2010 Gregory signed a 3 year contract with Israeli Premier League Club F.C. Ashdod. He resigned from Ashdod on 18 April 2011, with the club facing the possibility of relegation.
On 13 June 2011, Gregory was appointed the manager of Kazakh club FC Kairat from Almaty, Kazakhstan. Kairat survived relegation at the end of the 2011 season to the second tier of Kazakhstan football.
Gregory had his contract as manager of FC Kairat terminated in December 2011, and in April 2012 was paid $120,000 in compensation.
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