Centre forward Jimmy made his name scoring 5 goals on his debut in a replayed F.A. Cup game against Redhill during the Dons first Isthmian League season, but only played in four F.A. Cup ties (scoring two further goals) and one League match as he was also assisting Charlton Athletic as an amateur.

Described as a popular player and steady fellow, Jimmy went on to play for, amongst others, Millwall, Coventry City, Clapton Orient, Luton Town, Chelsea (where he was top scorer in 1927/28 and 1928/29), Norwich City, Sunderland, Fulham and Hull City. He also played for the Southern League representative XI, scoring twice in a 3-0 victory over the Central League.

He then moved into Non-League football with Tunbridge Wells Rangers and Peterborough United, signed for Tranmere Rovers, then played for Sittingbourne and Aldershot before retiring.

He managed Dartford FC and later worked as a scout at both Chelsea and Southampton, and is credited with having discovered Jimmy Greaves amongst others.