Derek started off his playing days at Northwood, breaking into the first-team at just 17, making his debut in a 2-0 home win against Brimsdown Rovers in August 1984. He was almost ever-present before making the move to Hayes in October 1985. By then he had made 47 appearances and scored 8 goals.

From there he went on to enjoy a professional career with Barnet, Southend United, Watford and Peterborough United, totalling just over 250 League and cup appearances and scoring twelve goals.

He dropped back into non-League with spells at Stevenage Borough, Dagenham & Redbridge, Hemel Hempstead and Flackwell Heath.