Dean Smith is an English professional football manager and former player who is the head coach of Major League Soccer club Charlotte FC.

The 1999 Football League Third Division play-off Final was an association football match which was played on 29 May 1999 at Wembley Stadium, London, between Scunthorpe United and Leyton Orient. It was to determine the fourth and final team to gain promotion from the Football League Third Division to the Second Division. The top three teams of the 1998–99 Football League Third Division, Brentford, Cambridge United and Cardiff City, gained automatic promotion to the Second Division, while those placed from fourth to seventh place in the table took part in play-offs. The winners of the play-off semi-finals competed for the final place for the 1999–2000 season in the Second Division. The losing semi-finalists were Rotherham United and Swansea City who had been defeated by Leyton Orient and Scunthorpe United respectively.