Darren started his career at Norwich City as a trainee playing alongside, among others, Craig Bellamy and Darren Eadie. He skippered the reserve side during his two years at Carrow Road.

He first joined Yeovil in August 2000 and immediately formed a partnership with Lee Johnson in the heart of the midfield. The pair complemented each other perfectly and were regarded as the best central midfield pairing in the division.

Darren won several caps for the non-league England XI with his consistent displays.The midfield dynamo chipped in with his fair share of goals and managed twelve in his first season at Huish Park. He was influential in the team's rise into the Football League and scored on the day promotion was clinched at Doncaster Rovers.

His form continued into the League and he helped Yeovil to the League Two title with displays that earned him a place in the League Two Team of the Year.After more than five years with Yeovil, he left to join Swansea City for £150,000 but his time there was racked with injuries and operations.

In November 2007, he rejoined Yeovil initially on loan for six weeks and impressed greatly, his spell coinciding with an upturn in form.He returned to Swansea when the loan agreement ended and re-signed permanently in July 2008 to link up once again with his best friend Terry Skiverton in the Yeovil team.

 In December 2008, Darren suffered serious injuries in a car accident near Yeovil. He is currently recovering from those injuries and made an emotional re-appearance as a substitute in the manager's testimonial in July 2009.