Career
He was a Chelsea youth team player before being released in August 2000 after making just two substitute appearances. he was loaned out to Plymouth Argyle in 1998 in order to gain first team experience. He joined the then Conference side Yeovil Town on professional terms. He was with Yeovil for three years, winning the Football Conference and the FA Trophy during his time with the Glovers.
After four seasons, he moved on from Yeovil, joining Aldershot Town in 2004.
With Aldershot, he played in the Conference play-off Final at the end of the 2004-2005 season, which Aldershot lost on penalties. He moved to Weymouth on a free transfer for the 2006-2007 season, before signing for rivals Dorchester Town in the summer of 2008.
On 15 January 2015, following the departure of manager Graham Kemp, Crittenden was placed in temporary charge of Dorchester Town on a caretaker basis. Crittenden was then appointed player-assistant boss to new player-manager Mark Jermyn.