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, it 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.

The new manager initially had little impact on a squad which clearly had little confidence, but with the opening of the transfer window in January, Wise was able to wheel and deal and there were plenty of arrivals and departures. United entered 2007 sitting in 23rd place in the Championship, and fell to the bottom of the pile on January 30 despite a 2-1 win at fellow strugglers Hull City.

Leeds occupied bottom spot until the end of March, but a five-game unbeaten run gave renewed hope of survival and after a late Lubo Michalik winner against Plymouth at Elland Road, Wise's men moved out of the bottom three. That didn't last, though, and defeat at Colchester the following Monday, after being 1-0 up, proved the beginning of the end, and three games later relegation was all-but confirmed following a 1-1 draw at home to Ipswich Town. 

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. With a 10-point deduction in place, United's relegation was confirmed with the administration coming on the eve of the final game of the season at Derby County.

The administration saga and legacy lasted throughout the summer of 2007 and well into the new season. Despite Bates' buy-back plans receiving creditor approval, the Inland Revenue lodged an objection with the court rendering the CVA invalid. The administrators (KPMG) immediately offered the club for sale again - and the bid from Bates was again accepted. But, without a valid CVA in place, the Football League deemed the club's exit from administration to be a breach of their insolvency policy and initially refused the club a share of league membership throwing into doubt its future.

That 'golden share' was finally handed back to the club less than two weeks before the start of the 2007/08 season, but it came at a price, with a 15-point sanction imposed by the League. The club lost an appeal hearing - the majority of Football League chairmen voting in favour of the punishment - and when Wise took his side to Tranmere on August 11, Leeds kicked off the season 15 points adrift at the foot of the table.

Amazingly, particularly considering Wise had been unable to make any signings until the share was returned, United won the first seven games of the season and were unbeaten in 13. But the departure of first team coach Gus Poyet preceeded what was a disastrous November and, despite United topping the table briefly on Boxing Day, the early season consistency was starting to wane. Neverthless, to start 15 points behind and hit top spot was a marvellous achievement for all concerned.

At the end of a frustrating January, Wise resigned from his post as manager to join Newcastle United as executive director (football). Former player Gary McAllister was immediately appointed as his replacement and his first game was a 2-0 home defeat at the hands of Tranmere Rovers. It took a month before McAllister recorded his first victory as boss - a Tresor Kandol goal securing the points at Swindon - but it was enough to kick-start the season and a late run saw United reach the Play-Offs.

Off the field and after months of asking, the club was finally granted an independent arbitration hearing into the 15-point sanction which was to take place in April. During the course of the hearing, a 2-0 win at Millwall would have been enough to secure promotion without the 15 points, but when the outcome was finally made public in May - two days before the final league game - it was ruled that the sanction would not be rescinded.

In the Play-Offs, United lost the first semi-final at home to Carlisle - a late Dougie Freedman goal reducing the arrears to 2-1 - but a marvellous performance at Brunton Park resulted in Jonny Howson scoring his second goal of the night - with the last kick of the game - to secure a 2-0 win and book a first trip to Wembley since 1996.

The final, however, proved a damp squib, and over 50,000 Leeds fams watched as Doncaster won the League One Play-Off final 1-0 to secure their place in the Coca-Cola Championship.

United re-grouped with a pre-season tour to Ireland and a handful of new signings in readiness for another assault on promotion. A six-game winning run in September fuelled optimism, lifting Leeds to second in the table, and with teenagers Fabian Delph and Aidan White both featuring regularly in the first team, the signs were looking good.

But a sudden loss of form away from home proved the pre-cursor to another disappointing November and, despite Jermaine Beckford hitting the 20-goal mark, a run of five successive defeats, including a 1-0 reverse at Blue Square Premier League (Conference) leaders Histon in the FA Cup second round proved the end of the road for McAllister.

The Scot parted company with the club on Sunday December 21, following a 3-1 reverse at MK Dons, and 48 hours later Simon Grayson was installed as the new manager at Elland Road. Grayson, a former trainee at Leeds, had guided Blackpool to their highest league placing in over 40 years after taking them into the Coca-Cola Championship in 2007.

Grayson immediately ended a run of five straight defeats - a last-minute goal from Robert Snodgrass secured a point against league leaders Leicester City on his first game in charge - and the United manager set up about kick-starting the promotion bid.

Grayson signed Leeds-born Richard Naylor from Ipswich Town to bolster his defence, but despite an improvement in performances, a 2-0 defeat at Hereford in February saw Leeds slip to ninth and the travelling fans made their feelings clear towards the team.

That game proved a watershed, though. United embarked on an 11-game unbeaten run and were still in with an outside chance of securing automatic promotion on the penultimate weekend of the season. Leeds won 11 successive home league games at home - the best run for over 40 years - and Jermaine Beckford became only the fifth player in the club's history to score 30 goals in a season as he clocked up 34.

The season ended in disappointment, however, as Grayson's side lost the Play-Off semi-final to Millwall 2-1 on aggregate. A 1-0 defeat at the Den was followed by a 1-1 draw at Elland Road - Jimmy Abdou scoring with the visitors only shot of the evening on target after Luciano Becchio had netted for United - and a third successive season in League One was facing the club.

Undeterred, Grayson and his squad recovered from the set-back to start the 2009/10 season with a club record eight straight wins in all competitions, and a 13-game unbeaten start to the league season gave United a platform in the top two.

Those early months also included a Carling Cup clash with Liverpool at Elland Road in which United went down 1-0, despite performing heroically in front of a sell-out crowd.

By Christmas, Leeds were nine points clear in the promotion places, and when 2010 started with an FA Cup third round win at Manchester United - the club's first win at Old Trafford for 29 years - the season was shaping up to be a memorable one.

Away performances at Bristol Rovers and Brighton had been the league highlights of the first half of the season and Grayson's men almost appeared to be cruising their way towards promotion.

But, despite gaining a 2-2 draw at Tottenham in the fourth round of the FA Cup, the league form took a dive. United were also knocked out of the Johnstone's Paint Trophy Area Final on penalties at Carlisle and when Swindon won at Elland Road in April, making it four straight defeats, the worst run under Grayson, Leeds slipped out of the promotion spots for the first time in eight months.

Suddenly, it was a four-horse race behind Norwich City with Swindon, Millwall, and Charlton all in with a chance of securing that second spot. Leeds could have clinched it on the penultimate afternoon at Charlton, but with five strikers on the pitch as Grayson's men pushed for victory, the home side nicked a late winner to leave it all to play for on the final day.

But Grayson's men summoned up one final push and promotion back to the Championship was secured on the final afternoon of the season, following a 2-1 win against Bristol Rovers in front of a full-house at Elland Road. United had been reduced to 10 men when Max Gradel was sent-off, and fell 1-0 down at the start of the second half. Jonny Howson replied with an equaliser, though, and Beckford scored the all-important second to secure Leeds a second promotion in the space of 20 years. The celebrations were truly memorable.

Beckford again scored 30 goals in the campaign, including the winner at Old Trafford and the strike that secured promotion, and he officially became the most prolific marksman of the modern era by becoming only the second Leeds player ever to score 30 in a season on more than one occasion.

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