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O'Leary's Leeds never finished outside of the top five, but following their defeat 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. Leeds signed Liverpool legend Robbie Fowler and Seth Johnson for large fees and big wages. However, Leeds narrowly failed to qualify for the Champions League losing out to 4th place to Newcastle United, 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 £30 million. 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, who Ridsdale had promised Venables would not be sold. Other star players such as Lee Bowyer, Nigel Martyn, Robbie Fowler, Robbie Keane and Harry Kewell were also sold over time, with Kewell's departure under rather acrimonious circumstances.

With tensions mounted between Ridsdale and Venables, as the team was still underachieving given the quality of players remaining and star player that had left. Venables chose to release the likes of Leeds' star players Olivier Dacourt and David Batty in the years prior. After a string of poor results and being in the bottom half of the table, Venables was sacked and replaced by Peter Reid. During this time Ridsdale had resigned from the Leeds board, and was replaced by existing non-executive director Professor John McKenzie. At this time Leeds were in danger of relegation, but managed to avoid the drop in the penultimate game of the season.

Reid was given a permanent contract at Leeds the following summer. Due to still being in financial torment players were sales and lack of funds meant they failed to land targets Paolo Di Canio, Patrik Berger and Kléberson. However, Reid brought in 8 players on loan which was not a success, with players such as Roque Júnior failing to live up to their reputations. An unsuccessful start to the 2003–04 season saw Peter Reid dismissed. Leeds were in turmoil after poor performances and restlessness from the club, Eddie Gray took over as caretaker manager until the end of the season. An insolvency specialist, Gerald Krasner, led a consortium of local businessmen which took over Leeds and under his chairmanship oversaw the sale of the clubs' assets, including senior and emerging youth players of any value. As the majority of the squad was sold, despite Gray's efforts as he was largely perceived blameless for Leeds' performance and relegation during the 2003–04 season, meaning their first out of the top flight after 14 years.

Following relegation, Gray's reign as caretaker manager was ended, and the then assistant manager Kevin Blackwell was appointed manager, his first managerial job in football. A mass exodus ensued as most of the remaining players were sold or released on free transfers to further reduce the high wage bill. Key players such as Mark Viduka, Dominic Matteo, Paul Robinson, Alan Smith and James Milner were all sold for relatively reduced fees. Blackwell was forced to rebuild almost the entire squad through free transfers. Leeds were eventually forced to sell both their training ground for £4.2 million, and their stadium in the autumn of 2004.[19][20]

The board finally sold the club to Ken Bates for £10 million.[21] Blackwell stabilised the team by signing players on free transfers and low wages with Leeds finishing the 2004–05 season mid-table in the Championship. At the end of that season defender Lucas Radebe retired after a series of injuries and promising young player Aaron Lennon joined Tottenham Hotspur. In the 2005–06 season Leeds finished in the top 6 and made the play-off final, after being in the top 3 for most of the season with Leeds' form drastically dipped in the last quarter of the season.

The 2006–07 season started badly with Leeds conceding late goals in several matches, and in September 2006, Blackwell's contract as manager of Leeds United was terminated. Leeds hired John Carver as caretaker manager but his spell was not a success and he was relieved of his duties with Dennis Wise being eventually installed as his replacement after a month without a permanent manager. Defender Matt Kilgallon left in January to join Sheffield United, and Wise was unable to lift the team out of the relegation zone for much of the season, despite bringing a number of experienced loan players and free transfers on short term deals into the squad. With relegation virtually assured, Leeds entered a Company Voluntary Arrangement (administration) on 4 May 2007, thus incurring a league imposed 10-point deduction which officially relegated the club to the third tier of English football.[22][23]

The relegation was the lowest point in the club's history, as Leeds United had never played any lower than the second tier of English football. The summer saw players such as David Healy and Robbie Blake leave, whilst long serving Gary Kelly retired after the relegation. Leeds, as they had after Premiership relegation three years previously, were forced to build a squad almost totally from scratch; with the future of the club uncertain Leeds could not sign any players until a few days before the opening game of the season against Tranmere Rovers.

It's really scary the similarities between Leeds and us.

*Gambled and missed out on champions league by 1 spot

* sold any players of worth to constantly slash wage bill

* David o Leary

* relegation

We could potentially be the next Leeds. In 5-10 years time people could be saying god look at Aston villa where did it all go wrong for them

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Yeah that seem's quite familiar. Two team's shared the same manager and we both got relegat..... What's that? We haven't been relegated yet?


Also nobody said we're in a sound financial position, just that it's better than Leed's was.  

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