The arrival of Harry Redknapp as manager during the next season saw O'Hara gradually lose his regular starting 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 2009, keeping him at White Hart Lane until 2013.