Out of Luck: Leeds United's 7 Most Gutwrenching Moments Since Relegation in 2004

The last 14 years have not been an easy ride for Leeds fans. Jumping from owner to owner, manager to manager, the turmoil witnessed at Elland Road nearly liquidated one of England's giants.

Things are now looking up for Leeds fans, however, with new chairman Andrea Radrizzani stabilising the club after a succession of calamitous owners. 

Leeds fans do not look fondly upon the club's fortunes from 2004 onwards, and here we assess the seven worst moments for the Yorkshire club since their relegation from the Premier League.

7. Selling Elland Road

After relegation in 2004, a consortium led by Gerald Krasner agreed to take the reigns at Elland Road and try to save the club from a potential liquidation. To help with crippling debts, Krasner agreed to sell Elland Road, Leeds' historic home, for a measly £10m.

Leeds would then have to pay rent to play at Elland Road which would peak at around £1.7m a year, but thankfully for Leeds fans, current owner Radrizzani has recently bought back Elland Road. The years without a proper home for Leeds epitomised how far the Whites had fallen.

6. Losing a Championship Play Off Final

Two years after relegation in May 2006, Leeds were within touching distance of getting back to where they belonged. They had reached the Championship play-off final after a great season ran on a shoestring budget, but they fell at the final hurdle.

Leeds lost 3-0 to Watford and, to rub salt into the wound, former Leeds loanee Marlon King, who wanted to sign for United, scored a goal in the final and was the league's top scorer that season. 

Surprisingly, the worst was yet to come for Leeds fans.

5. Relegation to League One

In 2007, Leeds entered administration and were deducted 10 points. Following this penalty, the Yorkshire giants were relegated to League One - the club's first ever foray in the third division.

To make matters worse, Leeds were once again on the brink of extinction after owing £6m to HMRC. One of England's giants, who had been in the Champions League Semi Final only six years prior, would now be travelling to Yeovil and Hereford on a regular basis.

Could things get even worse?

4. Losing a League One Play Off Final

Of course things got worse.

Despite entering League One with a fifteen point deduction at the start of the season, the biggest the FA had ever handed out to a club, Leeds started their season with a siege mentality that meant they had reached zero points within five games. 

Leeds continued their early season prowess and reached the Play Off Final against fellow Yorkshire outfit Doncaster Rovers. The Whites lost 1-0 thanks to a James Hayter header, and this defeat was arguably the lowest moment yet in Leeds' history.

However, things still got worse.

3. Losing to Histon

In November 2007, the (once) mighty Leeds United travelled to non-league Histon for an FA Cup tie many saw as a potential banana skin.

The banana skin prophecy was fulfilled as Leeds lost to Histon 1-0, with a postman scoring for the home side.

After what has been branded as one of United's worst ever results, nothing was looking positive for the Yorkshire club. Leeds United were at the lowest point ever in their eventful history.

2. A Succession of Awful Owners

Four calamitous owners in the space of a decade meant that Leeds' dismal performances on the pitch seemed minuscule in comparison to their off-field problems. Peter Ridsdale led United to administration in 2004 after a disastrous financial policy, and subsequent owner Ken Bates did little to appease fans, whom he branded 'morons' following protests against his ownership in 2011.

Bates finally sold the club in 2012 to Bahrain-based GFH, who promised to get Leeds back in the Premier League within two years. Despite GFH's promising rhetoric, their ownership was  mired by a poor financial running of the club, and they sold the club to Italian tycoon Massimo Cellino in 2014.

Cellino's time at the club was arguably the messiest of all owners, and the 'manager-eater' would even appoint the unknown Dave Hockaday as head coach, who would only last one month at Elland Road. Cellino would go through a staggering seven managers during his time at Leeds as they struggled in the Championship.

1. Selling Key Players

The talent Leeds have produced and then subsequently sold is heartbreaking for their fans.

In recent years, Leeds sold Luciano Becchio, Robert Snodgrass, Bradley Johnson and Jonny Howson all to Norwich alone. This, coupled with the sales of Sam Byram, Ross McCormack and Lewis Cook, has stunted any progress Leeds have made on the pitch, as the chopping and changing of their starting eleven has meant Leeds have been lurking in the Championship for the last eight seasons.

If Leeds want promotion back to the Premier League, then keeping their best players is a priority. United have been out of the top flight for the last 14 years, and however much progress they are making behind the scenes, the Whites need to build a team representative of the club's stature in English football.