 Ahead of the 2008–09 season, he signed a one-year contract extension with Middlesbrough in July 2008.On 17 October 2008, Craddock was sent on a one-month loan to Luton Town.This loan was extended in November after Craddock scored three goals in four games, Craddock's loan period came to an end in mid-January and Luton sought his services once more, this time lodging a bid of £80,000, which Middlesbrough accepted.