Leeds United’s fall from grace was spectacular. The Yorkshire club were rubbing shoulders with Europe’s elite in the Champions League one minute and being talked about as potential title contenders, but just a matter of months later crippling debts forced the sales of key players – often at a loss – and the inevitable happened when they were relegated in 2004.

As we all know, Leeds are yet to return to the top tier, even though many suspected their absence from the big stage would only be a short one. The years since have been no easier, with false dawns aplenty at Elland Road, while the current Massimo Cellino regime and his monthly sacking of managers has made the Whites a laughing stock. It really is a sad state of affairs for such a proud and historic club.

The crazy years of the late 1990s/early 2000s brought some huge transfers with them, and we thought it would be interesting to look back at some of these big-buys.

So, without further ado, here are Leeds’ most expensive players of all-time according to Transfermarkt…

10 – Michael Duberry (£5.74m)

Snapped up from Chelsea in 1999, Duberry lasted six years at Elland Road before being shipped off to Stoke, from where he went on a journey down the Football League before officially hanging up his boots in 2013. The Enfield-born centre-back was a decent player on his day, but shortcomings in his game were magnified during Leeds’ decline.

9 – Dominic Matteo (£6.06m)

Signed for just over £6m, Matteo provided a decent return for the money, making over 100 league outings in four years in Yorkshire. The defender was part of the 2004 exodus upon the Whites’ relegation from the Championship.

8 – Michael Bridges (£6.38m)

Widely held up as one of Leeds’ less successful signings, Bridges is, quite incredibly, still playing football for the amazingly-named Lambton Jaffas in Australia. The striker was talked up as one of the brightest prospects in England when the Whites prised him from Sunderland, but he never really got going at Elland Road in a period in which the team were not short of options up top.

7 – Darren Huckerby (£6.46m)

In 40 league games, Huckerby scored just twice and failed to live up to the £6.5m fee he commanded. He last around six months at Elland Road before moving on to play for Manchester City, whom were relegated in the 1999/2000 season.

6 – Mark Viduka (£7.78m)

Viduka was actually a real hit at Leeds and was one of their star men right up to the worrying drop into the second division. The Australian signed for the club from Celtic as a 24-year-old and was lauded for his barrel-chested style of play.

5 – Olivier Dacourt (£8.93m)

Unlike a few names on this list, Dacourt managed to escape the Leeds mess before relegation struck, departing the club in 2003 to join Roma. The Frenchman was a classy defensive midfielder who was very effective at the club’s peak.

4 – Seth Johnson (£9.78m)

Johnson was one of few players to stick around when Leeds were relegated in 2004, staying on for a full season before being released on a free transfer. All in all, the Yorkshire side didn’t get much for the near £10m they paid.

3 – Robbie Fowler (£14.28m)

Signed at the height of Leeds’ recklessness in 2001, Fowler was a once-great striker on a downward trajectory. The Liverpool hero cost a whopping £14.28m, and was seen as a guaranteed source of goals. However, he could only manage 30 league games between his arrival and 2003 exit.

2 – Robbie Keane (£15.30m)

Brought back from a fruitless spell in Italy, Keane was a hit at Leeds, staying at Elland Road through the 2001/02 season before joining Spurs in a £7m deal as the realities of the club’s crippling debts hit home.

1 – Rio Ferdinand (£22.10m)

Leeds eventually made a profit on Ferdinand when they sold him to Manchester United, but the huge fee paid for him was indicative of the madness at the club at the turn of the millennium. £22.10m was a huge fee, albeit the defender was a classy player.