Tottenham Hotspur Supporters Trust Breakthrough Award for his performances. He was further rewarded by a new three-year deal. The arrival of Harry Redknapp as manager during the next season saw O'Hara gradually lose his regular place in the league. He did however make a vital contribution in the club's League Cup semi-final tie against Burnley, as he scored one goal and helped create two more in a 4–1 first leg victory that helped see them through to the final. Unlike the previous year, O'Hara was included in their squad for the final. Coming on as a substitute, he also stepped up to take the first penalty kick in the shootout against Manchester United, after the match finished goalless; his effort was saved by Ben Foster as Spurs lost 1–4 on penalties. O'Hara signed a new contract in August, keeping him at White Hart Lane until 2013. Loan to Portsmouth After penning a new deal with Tottenham, O'Hara joined Portsmouth on loan until January 2010, with an option to remain at Fratton Park until the end of the season. He was a regular starter for Pompey during this time, but returned to Tottenham in January 2010 despite Portsmouth wanting to extend his loan and Tottenham agreeing to this, as Portsmouth were subject to a transfer embargo. Following the lifting of Portsmouth's transfer embargo weeks later, he returned to Portsmouth on loan for the remainder of the season. His loan spell created a conflict of interests when Portsmouth were drawn to play the winners of the Tottenham/Fulham tie in the FA Cup semi-finals. Tottenham manager Harry Redknapp gave a stern reminder to O'Hara that his ultimate loyalties lie with Tottenham after the midfielder admitted he hoped Spurs lost to Fulham as he would not be eligible to play against Tottenham. Tottenham did indeed progress to the semi-final, meaning O'Hara was denied a chance to play in the Wembley match. However, Portsmouth won the game 2–0 giving him a chance to play in the FA Cup Final where they were beaten 1–0 by Chelsea. At end of the season O'Hara was voted Portsmouth's Player of the Season for 2009–10. Having sustained a stress fracture during the 2009–10 season, it was announced in August 2010 that O'Hara was to undergo back surgery. This kept him out contention for any first team football until the New Year. Wolverhampton Wanderers On 30 January 2011, O'Hara joined