As a player, he was a versatile midfielder who started his career at Northampton Town and later played for Brighton & Hove Albion, QPR, Derby and Aston Villa.
He later managed Portsmouth, Plymouth Argyle, Wycombe Wanderers, Aston Villa, Derby County, Queens Park Rangers, Maccabi Ahi Nazareth, F.C.
[4] On departing from the Home Park club, he moved 300 miles north to play for Third Division Bolton Wanderers, making seven appearances before finally retiring as a player at the age of 36.
His first two professional spells in management (between January 1989 and June 1990), first with Portsmouth and then with Plymouth Argyle did not last long, with the latter being a caretaker appointment for just 2 games.
Shortly afterwards, he linked up as a non-contract player with his former England and Northampton Town teammate 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.
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.
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.
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.
[6] 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.
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.