Promotion, Champions, Champions League

In October 1988, with the team 21st in the Second Division, Bremner was fired to make way for Howard Wilkinson, who oversaw promotion back to the First Division in 1989-90. Under Wilkinson the club finished 4th in 1990-91 and then won the title in 1991-92. However, the 1992-93 season was a poor one, with Leeds exiting the Champions League in the early stages, and eventually finishing 17th in the League, narrowly avoiding relegation. Wilkinson's Leeds were unable to provide any consistent challenge for honours, and his position was not helped by a poor display in the 1996 League Cup final which Leeds lost to Aston Villa. Leeds could only finish 13th in 1995-96, and after a heavy home defeat to Manchester United early in 1996-97, Wilkinson had his contract terminated.

Leeds appointed George Graham as Wilkinson's replacement. The appointment was controversial as Graham had previously received a one year ban from the The Football Association for receiving illegal payments from a Football Agent. Graham made some astute purchases, and by the end of the season Leeds had qualified for the following season's UEFA Cup. In October 1998 Graham moved on to become manager of Tottenham Hotspur, and Leeds opted to replace him with assistant manager David O'Leary. O'Leary introduced promising youngsters, and under the coaching of Eddie Gray Leeds secured 3rd place in the league, sending the club into the UEFA Champions League. Unfortunately, Leeds' image was tarnished when players Jonathan Woodgate and Lee Bowyer were involved in an incident which left an Asian student in hospital with severe injuries. The resulting courtcase took nearly two years to resolve; Bowyer was cleared, and Woodgate convicted of affray and sentenced to community service.

In the UEFA Cup, Leeds reached their first European semi-final in 25 years and were paired against Turkish champions Galatasaray in Istanbul. Leeds lost the game, but the result was overshadowed by the death of two Leeds fans, Christopher Loftus and Kevin Speight, who were stabbed to death before the game. Leeds were only able to draw the return leg at Elland Road, thus going out of the competition. A minute's silence is held every year at the match closest to the anniversary of the incident to remember Christopher Loftus and Kevin Speight.

O'Leary's Leeds never finished outside of the top five, but following their appearance in the UEFA Champions League 2001 semi-final against Valencia their fortunes began to change. Under chairman Peter Ridsdale, Leeds had taken out large loans against the prospect of the share of the TV rights and sponsorship revenues that come with UEFA Champions League qualification and any subsequent progress in the competition. However Leeds narrowly failed to qualify for the Champions League, and as a consequence did not receive enough income to repay the loans. The first indication that the club was in financial trouble was the sale of Rio Ferdinand to Manchester United for approximately £30m. Ridsdale and O'Leary publicly fell out over the sale, and O'Leary was sacked and replaced by former England manager Terry Venables. Leeds performed badly under Venables, and other players were sold to repay the loans, including Jonathan Woodgate whom Ridsdale had promised Venables would not be sold. Tensions mounted between the pair, eventually resulting in the sacking of Venables, who was replaced by Peter Reid. By this time Leeds were in danger of relegation, but Reid saved Leeds from the drop in the penultimate game of the season. During this time Ridsdale had resigned from the Leeds board, and was replaced by economics expert Professor John McKenzie. An unsuccessful start to the 2003-04 season saw Peter Reid dismissed, and head coach Eddie Gray took over as caretaker manager until the end of the season.

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