Jamaican born Darren began his career in youth football at Bradford City, making his senior debut for them in March 2011, having been promoted to the first team squad just two days before. In August 2012 he moved to Southport, but then made a permanent move to Chorley in December 2012. He played 157 games for the Lancashire club, scoring 62 goals. More recently he played for Chester, joining the Deva outfit in November 2022, scoring 10 goals in 63 appearances.