Playing Career
Gregory made his professional football debut in 1972, at the age of 18, when playing for Northampton Town. He scored eight goals in 187 games over the next five years, before being transferred to First Division Aston Villa in 1977.
Gregory was a considerable success at Aston Villa. Despite playing two divisions higher than he had ever done before, he adapted well to First Division football and scored 10 goals in 65 games over the next two seasons. During his time at Villa, Gregory became the only player to play in every outfield position, wearing every number from 2 to 11 over his two seasons with the club, which remains a record.
In 1979, Gregory signed for Brighton & Hove Albion, who had just won promotion to the First Division for the first time in their history. He scored seven goals in 72 games over the next two seasons before dropping down into the Second Division to sign for Queen's Park Rangers.
He was part of the QPR side that reached the FA Cup final in 1982 (losing to Tottenham Hotspur in a replay) and won promotion to the First Division a year later as Second Division champions. He also helped QPR finish fifth and qualify for the UEFA Cup in 1984, but 1984-85 was a tough season for Gregory and his colleagues after manager Terry Venables departed to FC Barcelona and successor Frank Sibley was unable to keep up QPR's good form. At the end of a difficult season in which QPR only narrowly stayed in the First Division, Gregory dropped down two divisions to sign for fallen giants Derby County.
Derby County, champions of England in 1972 and 1975, had fallen into the Third Division in 1984 and had failed to win promotion in 1984-85. Gregory was the centerpiece of their midfield as they achieved promotion to the Second Division at the end of the 1985-86 season and to the First Division (as Second Division champions) a year later. Gregory stayed for one season as Derby County survived their first top flight season for nearly a decade, before announcing his retirement as a player. He played a total of 93 league appearances for the Rams, scoring 22 goals.
When taking over as manager of Plymouth Argyle early in 1990, Gregory re-registered himself as a player and appeared three times for them in the Second Division. 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.
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