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 ten points behind Bradford City (who were promoted in second place) and twenty-eight behind league winners Sunderland.

With six minutes of the match remaining, Michael Johansen volleyed the ball into the Ipswich goal, securing a 1–0 first-leg victory.

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.

Dyer's 90th minute headed goal made it 3–2 to Ipswich and level on aggregate, taking the match into extra time.

[3] 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.

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.

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.

[6] 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.

[8] 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.

"[10] 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".

[12] 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.

Four minutes later Taylor took the ball clear and his shot from 20 yards (18 m), under challenge from Rob Page, was straight at Alec Chamberlain in the Watford goal.

On 13 minutes, Eiður Guðjohnsen was challenged by both Robinson and Page, but the ball fell to Johansen whose shot went across the face of Watford's goal.

[20] Six minutes later, Guðjohnsen set off on a counter-attack, beating Robinson to go one-on-one with Chamberlain, but shot just wide of the right-hand post.

From the set piece, Neil Cox headed the ball clear, which fell to Wright whose overhead kick flew into the Bolton goal, making it 1–0 to Watford.

In the 89th minute, Watford doubled their lead: Kennedy won the ball from Sellars and passed it to Smart who side-footed it past Banks.

[24] Bolton ended their next season in sixth place in the First Division, qualifying for the play-offs,[25] where they lost in the semi-finals to Ipswich Town.