1999–2000 Gillingham F.C. season

The 1999–2000 season was Gillingham F.C.'s sixty-eighth season in the Football League. They gained promotion to the Football League First Division, after beating Wigan Athletic in the 2000 Football League Second Division play-off Final. Gillingham also had a successful FA Cup run, reaching the sixth round before being knocked out by Chelsea.

1999–2000 Gillingham F.C. season

The 1999–2000 season was Gillingham F.C.'s sixty-eighth season in the Football League. They gained promotion to the Football League First Division, after beating Wigan Athletic in the 2000 Football League Second Division play-off Final. Gillingham also had a successful FA Cup run, reaching the sixth round before being knocked out by Chelsea.