.jpg) The match took place at Wembley Stadium. | |||||||
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| Date | 31 May 1999 | ||||||
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| Venue | Wembley Stadium, London | ||||||
| Referee | Terry Heilbron (Newton Aycliffe) | ||||||
| Attendance | 70,343 | ||||||
The 1999 Football League First Division play-off final was an association football match which was played on 31 May 1999 at Wembley Stadium, London, between Bolton Wanderers and Watford. The match was to determine the third and final team to gain promotion from the Football League First Division, the second tier of English football, to the Premier League. The top two teams of the 1998–99 Football League First Division season gained automatic promotion to the Premier League, while those from third to sixth place in the table took part in play-off semi-finals; Bolton Wanderers ended the season fifth in the table, one position and one point ahead of Watford. The winners of these semi-finals competed for the final place for the 1999–2000 season in the Premier League. Birmingham City and Ipswich Town were the losing semi-finalists. Winning the final was estimated to be worth up to £10 million to the successful team.
The 1999 final was played in front of a crowd of 70,343 and was refereed by Terry Heilbron. Nick Wright put Watford ahead late in the first half with an overhead kick. Allan Smart doubled their lead with two minutes remaining and Watford won the match 2–0. As a result, Watford would play in the Premier League for the first time since its inception in the 1992–93 season. It also meant that Watford were promoted for the second successive season, having been champions of Division Two in the 1997–98 season. Elton John, Watford's chairman, watched the final from Seattle.
Watford were considered favourites for relegation the following season and finished bottom of the Premier League, 12 points from safety, having lost 26 of their 38 matches: they were relegated back to the First Division. Bolton ended their next season in sixth place in the First Division to qualify for the play-offs where they lost in the semi-finals to Ipswich Town.