On 18 July 2008, Kitson moved in a £5.5m move from Reading to Stoke City, breaking Stoke's record transfer fee.[8]
Having failed to score any goals in any of the 18 competitive games he played for Stoke City in the 2008–09 season, speculation arose as to whether Kitson was settled there or not. Chairman Peter Coates and manager Tony Pulis both denied any rumour that he might be leaving the Britannia Stadium.[9] The Stoke City board reacted to this growing disquiet, and he rejoined Reading on loan until the end of the 2008–09 season on 10 March 2009.[10]
Kitson later revealed that he made the "wrong decision" in joining Stoke, adding that he and his family were happy at Reading and that "I threw all of that away for what I thought was going to be a new challenge... I hold my hands up – it was my fault. I made the decision to go to Stoke, I didn't have to, no-one forced me to go, and it was a bad decision." With regards to his failure to score for Stoke, he said "I'd been bought for a lot of money but I wasn't sure I was being utilised in the way I thought I was going to be... You do have some days at training when you go back in and wonder what you're doing there."[11]
However, Reading failed to gain promotion, meaning that Kitson returned to Stoke. Kitson stated that he would "start his Stoke career again".[12] His first competitive goal for Stoke came in a 1–0 League Cup win at Leyton Orient on 26 August 2009.[13] He scored his first league goal for Stoke on 29 August 2009, which proved to be the winning goal against Sunderland[14] and then scored again with a goal against Bolton Wanderers.[15] However Kitson lost his place to James Beattie and joined Middlesbrough on a two-month loan.[16] He scored his first goals for Middlesbrough when he scored a brace against Peterborough United on 28 November 2009.[17] He returned to Stoke on 1 January 2010. He scored in the FA Cup against Manchester City and against Bolton. However, after a poor performance against Chelsea he never played for Stoke again and was branded as 'petulant' by manager Tony Pulis.[18]
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