He played for Darlington, Sheffield Wednesday, Birmingham and Chelsea in the Football League, making nearly 200 appearances in total.
[3] Having scored at a goal every two games for Darlington,[3] Gregg joined Sheffield Wednesday before the 1928–29 season, and contributed to them winning that year's First Division championship.
He moved on to Chelsea in September 1933 for a fee of £1,500, finishing his career with Boston United in the Midland League and with Sligo Rovers in Ireland during the Second World War.
[4] Gregg also made 1 WW2 Guest appearance for Clapton Orient on 26 August 1944, played at Fratton Park against Portsmouth, a 5–1 defeat, before a 10 000 crowd.
a report on the match in a local Portsmouth paper stated that Gregg had a shot on six minutes which was saved by the Pompey goalkeeper Harry Walker.