The 1999 Football League Second Division play-off Final was an association football match which was played on 30 May 1999 at Wembley Stadium, London, between Manchester City and Gillingham. The match was to determine the third and final team to gain promotion from the Football League Second Division, the third tier of English football, to the First Division. The top two teams of the 1998–99 Football League Second Division season gained automatic promotion to the First Division, while the clubs placed from third to sixth place in the table took part in play-off semi-finals; Manchester City ended the season in third position while Gillingham were fourth. The winners of these semi-finals competed for the final place for the 1999–2000 season in the First Division. Preston North End and Wigan A