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.

Watford finished the regular 1998–99 season in fifth position in the Football League First Division, the second tier of the English football league system, one place and one point ahead of Bolton Wanderers. Both therefore missed out on the two automatic places for promotion to the Premier League and instead took part in the play-offs, along with Ipswich Town and Birmingham City, to determine the third promoted team. Watford finished ten points behind Bradford City (who were promoted in second place) and twenty-eight behind league winners Sunderland.

Bolton's opponents for their play-off semi-final were Ipswich Town, with the first match of the two-legged tie being played on 16 May 2001 at the Reebok Stadium in Bolton. The visitors had a penalty appeal turned down by the referee late in the first half when Mark Fish appeared to trip David Johnson and the first half ended goalless. With six minutes of the match remaining, Michael Johansen volleyed the ball into the Ipswich goal, securing a 1–0 first-leg victory. The second leg took place at Ipswich's Portman Road three days later. The home team took the lead with a goal from Matt Holland on 14 minutes, but the score on the day was level after Bob Taylor's close-range shot went in. Ipswich were ahead once again one minute later through Kieron Dyer but a deflected strike by Per Frandsen made the score 2–2 with seven minutes remaining. Dyer's 90th minute headed goal made it 3–2 to Ipswich and level on aggregate, taking the match into extra time. Taylor scored his second and Bolton's third in the 96th minute, and Holland's 20-yard (18 m) strike made it 4–3 to Ipswich in the 116th minute. The tie ended 4–4 on aggregate with Bolton progressing to the final via the away goals rule.

Watford faced Birmingham City in their play-off semi-final and played the first leg at their home ground of Vicarage Road on 16 May 1999. After five minutes, Watford took the lead when Michel Ngonge headed Peter Kennedy's cross into the bottom corner of the Birmingham City goal to make it 1–0. Before half-time, Birmingham City's Chris Holland hit the outside of the post with a long-distance strike and Nick Wright's lob for Watford hit the crossbar. Midway through the second half, Tommy Mooney's header hit the Watford bar before Paul Robinson was sent off for receiving a second yellow card for a foul on Peter Ndlovu. No further goals were scored and the match ended 1–0 to Watford. The return match was played at St Andrew's in Birmingham four days later. Dele Adebola opened the scoring for Birmingham City after two minutes but David Holdsworth was sent off with more than an hour of the match remaining for a second yellow card. The first half ended 1–0, 1–1 on aggregate, and remained unchanged by the end of regular time. Half an hour of extra time went goalless forcing the match to be decided by a penalty shootout. At 6–6 with one penalty missed by each team, Watford's Alon Hazan put them ahead before Holland's miss condemned Birmingham City to defeat and sent Watford to the final.

This was Bolton's second appearance in the second tier play-off final; they had beaten Reading 4–3 after extra time in the 1995 final. Watford were making their first appearance in the second tier play-off final, but had lost to Blackburn Rovers in the 1989 play-off semi-finals. Bolton were aiming to make an immediate return to the top tier of English football having been relegated from the Premier League in the 1997–98 season on goal difference. Conversely, Watford were seeking back-to-back promotions, after ending the previous season as champions of the Second Division (third tier). They had been outside the top tier for eleven years. In the two regular season meetings between the two clubs, Watford had won both, defeating Bolton 2–1 at the Reebok Stadium in October 1998 and 2–0 at Vicarage Road the following April. Graham Taylor, the Watford manager, was making his first visit to Wembley Stadium since September 1993 in his last game as England manager. Reflecting on Watford's appearance at the national stadium in the 1984 FA Cup Final, he suggested: "There are two ways to go to Wembley. You either go as Watford did against Everton ... just happy to be there. Or you go to win." Elton John, Watford's chairman, also spoke similarly of the 1984 final: "Yes, we desperately wanted to win ... but there was something about getting there which was a victory in its own right for a relatively small club like ours". He went on to suggest that both Taylor and his team had an "overwhelming determination" to succeed in the play-off final.

Bolton's top scorer in the league was Bob Taylor who had fifteen goals for the season. Gifton Noel-Williams was Watford's leading marksman with ten league goals, but had not featured for his club since suffering a fractured hip in January. Mooney was second in the list of Watford's top scorers with nine league goals. The match was broadcast live in the UK on Sky Sports 2 with highlights shown later that evening on ITV. According to bookmakers Coral and Littlewoods, Bolton were favourites to win the match. The match was estimated in the media to be worth around £10 million to the winning team. The referee for the match was Terry Heilbron from Newton Aycliffe in County Durham.