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 Football League play-offs have been held every year since 1987.
In the First Division, Ipswich Town, who are aiming to return to the top flight after 5 years outside the top flight, finished 2 points behind second placed Manchester City, who in turn finished 2 points behind champions Charlton Athletic, who returned to the top flight after being relegated last season.
Bolton Wanderers, who as well as Barnsley are aiming to return to the top flight after relegation 2 seasons ago, finished 1 point behind Birmingham City in sixth place.