In the 2007–08 season, Craddock made a handful of first team appearance at Middlesbrough following a crisis of striker's injury and made two more league appearance for the club. However, Craddock suffered a hernia injury that resulted him having two operation and upon return, his first team opportunities was further limited. On 13 February 2008, Craddock joined League One side Hartlepool United on a month's loan. Craddock made his Hartlepool United debut three days later, where he played 26 minutes, in a 1–1 draw against Cheltenham Town. After making four appearance, Craddock's loan spell with the club came to an end on 18 March 2008 following a one-month loan.