Mossy started his career as a trainee at Chester and made his début for the club in November 1998, before going on to play 62 games for them.

In June 2001, Darren joined Town on a free transfer, and was one of our few key players the show any form as we endured a poor 2002-03 campaign which saw us relegated from the Football League. He continued his good form in the Conference during 2003-04 as Salop immediately won promotion back to the Football League. A notable moment for Moss was scoring the winning penalty in the Conference play-off semi-final against Barnet.

Darran's good form attracted interest from other clubs and in March 2005 he joined Dario Gradi at Crewe Alexandra, the north-west based club buying him for £170,000. A combination of injuries and then the signing of Jon Otsemobor from Rotherham left Moss with limited first team opportunities.

In May 2007, Moss re-joined Town on a free transfer and made 31 appearances last season with 2 goals against Wrexham and Chester.