After leaving school at 14, Derek played with Pat Field at Churchfield Old Boys for a season before joining Beckenham Town, where he played either side of his National Service. Turning down offers of a professional contract with Millwall, Orient and Crystal Palace - playing in the Midweek League for the latter, he moved to Wimbledon in the early 1950s. After making three appearances in the 1953/54 season he had to wait a couple of seasons, playing mostly in the 'A' and reserve teams, before returning to first team duty, becoming a regular during the 1956/57 and 1957/58 seasons. He was captain for a few games in 1957 helped the Dons to the South of Thames and Surrey Senior Cup finals, making a handful over 100 appearances before he slipped out of the first team as John Martin made the right-back berth his own.