The 2008–09 season was the seventy-seventh season in which football club Gillingham F.C. competed in the Football League, and the fifty-ninth since the club's return to the League in 1950. Gillingham finished the season in fifth place in Football League Two, gaining promotion to League One through play-off victories over Rochdale (over two legs) and Shrewsbury Town. The club also reached the third round of the FA Cup, before being defeated by Aston Villa.