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.