Darren Rolph began his footballing career in the same Norwich City youth side as Ruel Fox. He joined King's Lynn whilst still a teenager before joining Football league side Barnsley in August 1987. After a handful of first team appearances for the Tykes, he returned to the non-league arena with Frickley Athletic and Gainsborough Trinity.

By the time he rejoined King's Lynn, his reputation as a hard tackling centre back earned him the nickname "Pitbull". He joined Dr Martens league side Sudbury Town in 1994 but has experienced knee injuries that have required operations thus limited his appearances for the Suffolk side to 75 games (2 goals). In the summer of 1997, he joined Wisbech Town who also fielded ex-Canary Lee Bray .

Darren quit Wisbech in March 1998 to join Eastern Counties league side Ely City. In July 1998, he switched to Fakenham Town.