His start to the 2007–08 season began with two goals in consecutive wins against Wigan Athletic and Tottenham Hotspur. His appearance in the starting 11 for Everton was threatened by the arrival of South African loan-signing Steven Pienaar. Osman scored his first goal in a UEFA competition on 25 October 2007, Everton's second in a 3–1 UEFA Cup group stage win over Greek club Larissa at Goodison Park. His shot from 22 yards helped Everton to the top of the group and was voted Everton's Goal of the Season. Osman scored both goals in Everton's 2–0 win over Fulham on the final day of the season to secure Everton 5th place in the Premier League for 2008–09. At the end of the season, he started in the 2009 FA Cup Final at Wembley Stadium, being replaced by Dan Gosling in the 82nd minute of the 2–1 defeat to Chelsea.