Gaizka Mendieta hits Valencia's third goal in the 2001 Champions League semi-final
On the final day of the 2000-2001 campaign, Leeds, Liverpool and Ipswich were battling it out for the last Champions League place in the Premiership.
That tussle came only days after the Elland Road outfit missed out on a spot in the final of that European competition following a last-four defeat at the hands of Valencia.
Liverpool eventually triumphed in the race to clinch third place in the table behind Manchester United and Arsenal, leaving the clubs from Yorkshire and Suffolk to contest the Uefa Cup.
Fast forward to this season and Leeds, who also just missed out on qualifying for the Champions League in 2001-2002, have been relegated to League One after going into administration.
Also in the shake-up for the Uefa Cup places in 2001 were Chelsea, who did qualify in sixth place and who have since gone on to win two Premiership crowns, and Sunderland, who missed out on Europe in seventh but have won promotion to the top flight this season.
BBC Sport looks back on the factors that have contributed to the downfall of Leeds, who have entered the third tier of English football for the first time in their history.
The failure to qualify for the Champions League during the 2000-2001 and 2001-2002 seasons led to dire financial consequences for Leeds.
In March 2002, the club announced pre-tax losses of £13.8m for the final six months of the previous year, with the failed £100m gamble on players in a bid for European success beginning to make the accountants nervous.
Peter Ridsdale welcomes new £7m signing Seth Johnson in 2001
Chairman Peter Ridsdale sanctioned the spending spree by manager David O'Leary but, despite initially insisting he would ride out the increasing storm at the club, he resigned his role in March 2003.
Professor John McKenzie replaced Ridsdale at the helm but in October 2003, Leeds posted pre-tax losses of £49.5m for the year ending 30 June 2003, which was a record annual loss for a British football club.
Leeds averted the threat of going into administration by signing an agreement with the creditors before Professor McKenzie, who had put a price tag of £60m on the club, resigned as chairman and then as a director.
A locally-based consortium led by new Leeds chairman Gerald Krasner sealed a £30m takeover in March 2004 but by November of the same year Elland Road had been sold on a sale-and-lease-back arrangement after a buy-out led by Sebastien Sainsbury failed.
Former Chelsea supremo Ken Bates then stepped into the breach by buying a 50% stake in the club in January 2005.
Little did O'Leary know when the club failed to qualify for the Champions League in 2001 and 2002 on the back of his £100m outlay for players that the loss of television rights and sponsorship benefits they could have earned would have such a catastrophic effect.
After nearly four years in charge he was sacked in June 2002.
Former England boss Terry Venables became Leeds manager in July 2002 but by the end of the year the fans were calling for him to go because of poor Premiership form and a Uefa Cup exit at the hands of Malaga.
Venables himself hinted that he may have to consider his future if more players were sold so it was no surprise when he left Leeds in March 2003 and former Sunderland boss Peter Reid took over.
However, with Leeds bottom of the Premiership in November 2003, there was an inevitable parting of the ways after a 22-match reign. It was left to caretaker boss Eddie Gray to oversee the descent into what was then Division One in 2004 - after 14 years in the top echelon of the English game.
He was then replaced by Kevin Blackwell in what was seen by some as a surprise appointment, with many other bigger names being linked to the post.
Wise was unable to prevent Leeds' drop into League One
However, with no money, few experienced players and seemingly little hope he managed to instil a team spirit and a work ethic into the side that - after a mid-table position in 2004-2005 - propelled them to fifth place in the Championship last season.
After years of uncertainty the fans were given renewed hope that this was to be the springboard for success but Watford ended all that with victory over Leeds in the play-off final.
Despite that setback, Leeds were still touted as one of the candidates for promotion this season but Blackwell was sent packing in September 2006 after a poor start to the campaign.
A month later, Dennis Wise left Swindon for Elland Road and even though he turned the relegation battle from a seemingly doomed scenario into a down to the wire one, he was unable to stop the rot and next year supporters will be having to learn the routes to new destinations in League One.
The financial plight at Elland Road led to the cut-price sale of some of the club's assets - ie the players.
The exit of defender Rio Ferdinand to fierce rivals Manchester United left fans angry and disappointed but at least when he was sold in July 2002, Leeds were left with the £30m in the coffers they had craved.
However, when, in 2003, BBC Sport analysed other departures the findings were very different. Striker Robbie Keane joined Tottenham in an eventual £12m deal in August 2002 - only 15 months after arriving from Inter Milan for £12m, while the £10m-rated duo of Lee Bowyer and Olivier Dacourt joined West Ham and Roma for £100,000 and £3.5m respectively.
Manchester City bought forward Robbie Fowler, who Leeds signed from Liverpool for £11m in 2001, for £6m in January 2003.
Meanwhile, £15m-rated Jonathan Woodgate and Harry Kewell, who had progressed from the trainee ranks at Leeds, sealed respective £9m and £5m moves to Newcastle and Liverpool in the January and December of 2003.
How the Premiership top seven in 2000-2001 have fared since
The big-name departures did not stop there. In July 2004, striker Mark Viduka joined Middlesbrough for £4.5m, while in May of the same year Tottenham acquired goalkeeper Paul Robinson for £1.5m and Manchester United snapped up striker Alan Smith in a deal worth £7m.
The financial implications of relegation have led Leeds to urge any would-be investors to prove they have the funds in place to help the club bounce back to the Championship
Chairman Ken Bates has given his backing to Dennis Wise but if the former Chelsea player remains as manager he faces a battle to keep his best players. Plus, if any exits reap monetary rewards how much of that will he be given to plow back into rebuilding the squad in a bid to clinch a quick promotion?
Leeds striker David Healy, who has already been linked to Rangers, has made a big impact on the world stage with Northern Ireland this season but will he and his team-mates remain content at a club with a big history yet facing life in a division that generates smaller column inches in the media?
The club may also have to contend with a fight to keep the fans coming through the turnstiles.
None would have expected a return to the glory days under manager Don Revie of the 1960s and 1970s but after last season's near miss on the promotion path the supporters must be stunned by the drop down a division.
Manchester City were relegated to the same division in 1999 - then called Division Two - and bounced back a year later with a play-off final victory that eventually led to a return to the Premiership so, if Leeds can climb off the management merry-go-round and look to long-term stability at the helm, all may not be lost.
Former Leeds manager O'Leary recently told BBC Five Live Sport that he hoped the club would stave off relegation because "I never wanted to leave, the fans were fantastic to me and I had great times there".
If Leeds had gone on to reach that Champions League final six years ago or been involved in the competition the following season the fate of the club could have been so different.