The Football League play-offs for the 1998âÂÂ99 season were held in May 1999, with the finals taking place at the old Wembley Stadium in London. The play-off semi-finals were played over two legs and contested by the teams who finished 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 went through to the finals, with the winner of the matches gaining promotion for the following season.
The Football League play-offs have been held every year since 1987. They take place for each division following the conclusion of the regular season and are contested by the four clubs finishing below the automatic promotion places.
In the First Division, Ipswich Town, who were aiming to return to the top flight after a 4-year absence, finished one point behind second placed Bradford City, who in turn finished 18 points behind champions Sunderland, who returned to the top flight after being relegated two seasons previously. Birmingham City, who were aiming to return to the top flight after 13 years outside the top division, finished in fourth place in the table. Watford, who were aiming to return to the top flight for the first time since 1988, finished in fifth place. Bolton Wanderers, who were aiming to return to the top flight after relegation the previous season, finished one point behind Watford in sixth place.
Ipswich Town 4âÂÂ4 Bolton Wanderers on aggregate. Bolton Wanderers won on away goals.
Birmingham City 1âÂÂ1 Watford on aggregate. Watford won 7âÂÂ6 on penalties.
Gillingham won 2âÂÂ1 on aggregate.
Manchester City won 2âÂÂ1 on aggregate.
Rotherham United 0âÂÂ0 Leyton Orient on aggregate. Leyton Orient won 4âÂÂ2 on penalties.
Scunthorpe United won 3âÂÂ2 on aggregate.