Lewis started the 2008–09 season as the team's second leading scorer, earning an appearance in the 2009 NBA All-Star Game. In the 2009 NBA playoffs, Lewis hit a game-winning shot in the first game of the Eastern Conference Finals against the Cleveland Cavaliers, what he called the biggest shot of his career. The Magic won the series and advanced to the NBA Finals, where they were defeated by the Los Angeles Lakers in five games.