Birmingham born winger Jack Gregory joined non league Willenhall Swifts in 1911 and soon thereafter joined Southern League Champions Queen’s Park Rangers in 1912, playing for them both sides of the First World War, during which he served in the Armed Forces. After the end of the War, he returned to Loftus Road and when after a final Southern League season they joined the Football League he played in Queen’s Park Rangers’ inaugural Football League match in Division Three (South) against Watford in August 1920, contributing 15 goals during their first League campaign and missing only 5 games in their first two League seasons. He was part of QPR’s giant killing team that beat First Division Arsenal 2-0 in their January 1921 FA Cup tie.
His final season at Rangers was 1922-23, in which he remained a first team regular, when after 23 goals after 118 games since joining the Football League he moved to become player-manager of Southern League Yeovil & Petters United becoming their first professional manager in May 1923.
He led Yeovil to the Western Section Championship of the Southern League in 1923-24 and continued as their player-manager until he resigned in May 1928. Under Gregory’s leadership The Glovers first became a giant killing force in the FA Cup, playing their first ever game against a Football League team when they beat Division Three (South) Bournemouth & Boscombe Athletic 3-2 at Huish Park in the final qualifying round in front of a crowd of 5,500 in November 1924 to enter the First Round proper of the competition for the first time, where they lost 4-2 at home to Bristol Rovers in front of 6,600 spectators, finishing the match with only eight men due to injuries.