2000s
David O'Leary took to football management like a duck to water. Everything seemed to fall into place. Money was made available and new arrivals included Oliver Dacourt, Dominic Matteo and Mark Viduka - and, later in the season, West Ham defender Rio Ferdinand for £18m - a world record for a central defender.
Alan Smith was on target twice in the Champions League qualifying game against TSV 1860 Munich which put United into the competition proper. The draw for the group stages placed United alongside such clubs as Barcelona, AC Milan and Besiktas. The group of death, it was claimed.
It certainly was a tough looking group and when United suffered a 4-0 defeat in Barcelona it looked even tougher. But O'Leary's side shocked most people when in successive home games they beat AC Milan 1-0 and then put six past Besiktas, forcing people to sit up and take notice.
A draw against Besiktas in Turkey, a home draw with Barcelona and a draw in Milan was enough to put United into the next stage of the competition. Again they were placed in a fantastic group, this time alongside Real Madrid, Lazio and Anderlecht - another so-called Group of Death.
United emerged from this, too, and drew Deportivo La Coruna in the quarter-final. They eased past the Spanish side 3-2 after having won the first leg at Elland Road 3-0 but went out of the competition at the next stage, losing to Valencia on a 3-0 aggregate scoreline.
In the Premiership, United had to settle for fourth place and a UEFA Cup spot for the 2001-2002 season. O'Leary had increased his squad with the signings of Robbie Fowler from Liverpool and Derby's Seth Johnson.
And with young players such as Jonathan Woodgate, Paul Robinson, Alan Smith, Ian Harte, Harry Kewell, Michael Bridges and Lee Bowyer alongside Mark Viduka, Rio Ferdinand, Olivier Dacourt, David Batty, Lucas Radebe, Eirik Bakke, Robbie Keane, Nigel Martyn, Dominic Matteo and Fowler, United looked a real force to be reckoned with.
It wasn't all good news, however, as Bowyer and Woodgate had been involved in a court case concerning an assault on a student outside a Leeds city centre nightclub and though eventually Bowyer was cleared of all charges, Woodgate was found guilty of affray and ordered to do 100 hours community service.
The whole affair heaped bad publicity on the club and while United chairman Peter Ridsdale had come out publicly and said that it wasn't the club that was on trial ii didn't help when the publication of a book by the manager was entitled Leeds United on Trial.
Results on the field suffered and United finished the 2001-2002 campaign in fifth place. They went out of the UEFA Cup at the fourth round stage and were beaten 1-0 at Cardiff in the FA Cup third round. United won only seven of their remaining 17 league games after that cup exit. Hardly the sort of season you would expect from a side with so many good players in it.
Almost £100m had been spent on players with some £66m being recouped by the sale of players who were surplus to requirements. O'Leary had taken United to two European semi-finals and had kept United in the higher echelons of the Premiership during the four seasons he was in charge but with the club having invested so heavily in players, a Champions League income was essential. Sadly, United had fallen just short.
Having failed to qualify for the lucrative Champions League, it seemed likely that some players would have to be sold before the start of the 2002-2003 season. Chairman Peter Ridsdale and his board decided that O'Leary would be the first man out of Elland Road. The Irishman was sacked from his job in June 2002.
Terry Venables succeeded him but had a difficult time. Mounting debts resulted in the club allowing Rio Ferdinand to leave for Manchester United in a £30m transfer deal and Jonathan Woodgate was sold to Newcastle United to raise more funds while Robbie Fowler joined Manchester City.
On the field United dropped into the lower reaches of the Premiership and went out of the League Cup at the first hurdle and the FA Cup at the sixth round stage, beaten both times by Sheffield United.
It was a depressing time and with relegation a real threat Venables was dismissed in March 2003. Peter Reid was brought in as interim manager. He had eight games in which to save United from relegation and he achieved that with a game to spare, United pulling off a remarkable 3-2 away win against title chasing Arsenal, with goals from Harry Kewell, Ian Harte and Mark Viduka.
The club announced debts of nearly £80m and Ridsdale resigned as chairman to be replaced by Professor John McKenzie.
Having saved the club from relegation, Reid continued at the helm but following a string of poor results including a 6-1 defeat at Portsmouth in early November 2003, he was dismissed. Eddie Gray was given the job of trying to save the club from relegation. It proved an impossible one and United lost their Premiership status.
The financial situation at the club was critical, players had been sold and offloaded in a bid to reduce the wage bill and Trevor Birch, a former Ernst & Young turnaround specialist, had been brought in to sort out a debt restructuring as the club faced the possibility of going into administration.
In March 2004, Gerald Krasner, led a consortium of local businessmen, David Richmond, Simon Morris, Melvin Helme and Melvyn Levi in a take over of the club. Difficult decisions lay ahead.
More highly paid players had to be sold and Paul Robinson, Mark Viduka, Dominic Matteo, Alan Smith and James Milner were among those to leave the club. To raise more money the new board sold the Elland Road Stadium and the Thorp Arch training complex.
Kevin Blackwell, who had joined United as assistant to Peter Reid, took over from Gray as manager. Gary Kelly and Michael Duberry survived the summer 'cull' and new players, on much smaller salaries, were brought in. Defenders Paul Butler, Clarke Carlisle and Sean Gregan, goalkeeper Neil Sullivan and midfield man Jermaine Wright were among them.
In January, however, and amid rumours that the club was close to going into administration - or worse - Ken Bates moved in with a rescue package.
Blackwell continued as manager and his side, which had taken time to settle in, was boosted by the signings of strikers David Healy and Rob Hulse but still had to settle for 14th place in the Championship.
United made a steady if unspectacular start to the 2005-2006 season but their campaign gathered momentum as the season progressed and after briefly flirting with the possibility of clinching an automatic promotion place had to be content with a play-off place, after finishing fifth.
A 3-2 aggregate victory over Preston sent United to the Millennium Stadium play-off final against Watford. An estimated 40,000 United fans were in the stadium that day - tremendous backing and a pointer to the huge fan base the club have - but, sadly, it ended in failure, Watford winning 3-0.
The massive disappointment of that defeat was seemingly carried on into the 2006-2007 season, which turned out to be the worst in the club's 87-year history. Relegation to League One - the first time United had been in the third tier of English football - was the outcome of a disastrous season.
Blackwell was dismissed as manager and his assistant John Carver took over but his brief reign ended in his fifth match - a 5-1 defeat at Luton. United were in 23rd place in the Championship when former Chelsea and England midfielder Dennis Wise was brought in as manager.
With debts of £35m the club entered into administration on May 4 2007, after the Inland Revenue served up a winding up notice, although chairman Ken Bates had a buy-back deal approved by the club's creditors at a meeting the following month.
