On July 1, 2009, Boucher agreed to a two-year contract with the Philadelphia Flyers to be the steady, veteran backup to the starting goaltender Ray Emery. However, when Emery incurred an injury midway through the season, Boucher was thrust into the spotlight with mediocre results. A hand injury soon pushed Boucher to the sideline, and he was replaced by third-string goaltender Michael Leighton. Leighton excelled in Boucher's absence, and once healthy, Boucher found himself backing-up Leighton. Upon the return of Emery, Boucher was further demoted to the press box, with Leighton now the backup. Emery soon re-injured himself, giving Boucher a chance to back-up Leighton, who once again was playing well. Near the end of the season, with only 13 games left, Leighton went down with a high-ankle sprain, and Boucher was back into the spotlight for the Flyers once again. After a 2–1 shootout victory in the final game of the season against the New York Rangers, Boucher and the Flyers advanced to the playoffs.