Born in Darlington, County Durham, Craddock came through the youth system at Middlesbrough since joining the academy from Darlington Spraire Lads when he was eleven years old, and was a member of their FA Youth Cup winning side in 2003–04. While at the academy, Craddock suffered a serious shoulder injury, but managed to overcome the injury and started out as attacker role and then switched to defense role before reverting to attacker role. On 12 March 2005, Craddock signed his first professional contract with the club.