Garry Monk is the latest manager to try his luck at taking the Elland Road outfit back to the top flight but the early signs are that it is well within their grasp
Liverpool hosting Leeds was, for many a decade, one of the standout fixtures of any campaign. Though not traditional rivals, two pillars of English football facing off was an event not to be missed but it is now over 13 years since the Whites embarked along the M62 for a trip to Anfield.
That run will be brought to an end on Tuesday evening as Garry Monk's side pit their wits against Jurgen Klopp's title-challengers with a place in the semi-finals of the EFL Cup at stake. After years of missed opportunities, relegations, administrations and countless changes of personnel both on the pitch and in the dugout, these are the matches for which Leeds supporters live and, if recent form is to be continued, they could yet be once again getting used to facing off against the country's elite on a more regular basis.
Monk's arrival in the summer brought with it a wave of expectation following his encouraging start to life as a manager at Swansea City and, after a sticky opening few weeks, he has instilled a belief among the Elland Road faithful that has not been seen since they reached the Champions League semi-finals in 2001.
Having suffered just one defeat in their last six league matches, they have climbed into the Championship play-off places for the first time since December 2013. After two seasons of upheaval under the watchful eye of madcap owner Massimo Cellino, there is already a sense of relative stability, with the majority of the inexperienced Italian misfits brought in following Cellino's takeover now moved onto pastures new. In their place are a series of experienced Football League players combined with a number of talented academy graduates.
Striker Chris Wood has put an inconsistent first season behind him to find the net on 12 occasions in all competitions while former Valencia playmaker Pablo Hernandez has earned a reputation as one of the most creative players in the division. Behind them youngsters Kalvin Phillips and Ronaldo Vieira have impressed in midfield as they embark on their first full seasons in the senior squad while centre-back Pontus Jansson has earned himself cult status within just three months following his arrival on loan from Torino.
Fellow summer arrivals Kyle Bartley, Luke Ayling and Eunan O'Kane have added solidity to a previously fragile squad and, with Monk's no-nonsense style working to calm expectations as well as build a far stronger mentality among his players, the belief that Leeds could yet return to the top flight come May is not as misplaced as it previously might have been.
It could all have been so different if some reports are to be believed. It was rumoured back in August that Cellino's notoriously itchy trigger finger was preparing for its latest victim, with some even suggesting that had Marcus Antonsson not equalised in the closing stages against Fleetwood Town during just Monk's second game in charge then he would have faced the sack.
Cellino's unpredictable nature means that getting too carried away is not an option for most Leeds fans despite their fine form and, though it seems that his reign at the helm may come to an end in the near future as reports of a takeover intensify, the worry that Monk's whole project could yet come crashing down is a real one.
There is also the risk that the club continue to lose their best young players, with the lack of resistance in allowing the finest academy products to depart in recent years a real bugbear of those who pay their money to watch the team week in, week out. Jonny Howson, Fabian Delph, Sam Byram and Lewis Cook have all left to play Premier League football in recent years and left-back Charlie Taylor looks set to follow them this summer when his current contract runs down. In fact, Liverpool may use Tuesday's game to scout the 23-year-old, given their own issues in that position.
Whether promotion can persuade him to sign a new deal and stay remains unclear but for now he and the rest of the Leeds squad must concentrate on remaining in the hunt for at least a play-off spot. Though history and fanbase only count for so much in the modern game, Leeds being back in the big time would certainly not be something many supporters would begrudge given the length of time for which they have been away.
Climbing back to the Premier League is certainly not beyond them this term and, though ending Liverpool's long unbeaten run would be a huge shock, it may not be too long until they are back on Merseyside on a more level footing.