The Football League play-offs for the 1999–2000 season were held in May 2000, with the finals taking place at the old Wembley Stadium in London for the final time. The play-off semi-finals will be played over two legs and will be contested by the teams who finish in 3rd, 4th, 5th and 6th place in the Football League First Division and Football League Second Division and the 4th, 5th, 6th and 7th placed teams in the Football League Third Division table. The winners of the semi-finals will go through to the finals, with the winner of the matches gaining promotion for the following season.