The 2014–15 season saw Leeds United competing in the Championship (known as the Sky Bet Championship for sponsorship reasons) for a fifth successive season.

A summer that saw the departure of manager Brian McDermott in favour of the unheralded David Hockaday (whose only prior managerial experience was with Conference side Forest Green Rovers), as well as a host of players including club captain and top scorer Ross McCormack and dependable striker Matt Smith shipping out of Elland Road, saw Leeds listed as second-favourites for relegation (ahead of only a Blackpool side who were somehow in even more turmoil both on the pitch and off it) among most bookmakers. Their start to the season did little to dispel these predictions, with Hockaday sacked the day after a humiliating League Cup exit to West Yorkshire rivals Bradford City, on top of losing three of his first four league matches in charge. Sporting journalists were quick to note that his six competitive matches in charge were two fewer than Brian Clough had managed during his infamous 44-day spell as manager.

Academy manager Neil Redfearn took over as caretaker manager and earned 10 points from the next four games, putting Leeds in mid-table, but was overlooked for the permanent manager's job in favour of another unexpected candidate, Slovenian manager Darko Milanič. Milanič failed to win any of his six games in charge, however, and was himself sacked 32 days later, exceeding both Clough's and Jock Stein's joint-record as the club's shortest-serving manager.

With Leeds right back in relegation trouble, they turned once again to Redfearn, and while they remained dangerously close to the foot of the table until well into the New Year, a strong run of form between late January and the end of March propelled them out of danger (as with the previous season, they were also helped by the poor form of all the bottom three clubs). However, the sudden suspension of Redfearn's assistant, Steve Thompson coincided with a poor end to the season and contributed to Redfearn's falling out with Cellino. After the season ended, Cellino first attempted to demote Redfearn back to his prior role as academy manager, then sacked him altogether, leaving Leeds looking for their sixth manager since the departure of Simon Grayson three years prior.

Background and club ownership On 12 April 2013, Brian McDermott was appointed as Leeds United manager on a three-year contract. In the summer of 2013 McDermott updated the squad with £1 million midfielder Luke Murphy from Crewe Alexandra, and defender Scott Wootton from Manchester United. He further added to this by completing several free transfers including forwards Noel Hunt and Matt Smith in July, and Lithuanian international defender Marius Žaliūkas in late October. However, McDermott stuck with largely the same squad from the previous season. McDermott's side began the season slowly with a succession of draws and losses; however, a surge of form through October to December saw Leeds reach a high of 5th place in the table. By the end of January the club had dropped to 12th in the league however, and were winless in eight matches.

In January 2014 speculation grew that Leeds would be subject to takeover by Italian entrepreneur and Cagliari owner Massimo Cellino. A delegation representing Cellino was seen at Elland Road and the Thorp Arch training ground several times, and on 28 January it was reported that Cellino had asked for his associate and former Middlesbrough defender Gianluca Festa to sit in the dugout for Leeds' 1–1 draw with Ipswich. On 31 January it was reported that McDermott had been sacked as manager of the club, with Gianluca Festa speculated in the media to be his most likely replacement. The following day reports emerged suggesting Gulf Finance House club directors were attempting to reinstate McDermott as manager, saying the Cellino family (the club's prospective new owners) had no authority to dismiss him. In an interview in December 2023, Cellino revealed he had asked for the couch to be replaced rather than the coach and he had been misunderstood.Ex-Leeds United owner Massimo Cellino admits huge manager sacking 'mess', it's beyond belief The following day, assistant manager Nigel Gibbs was named as caretaker manager for the club's home derby against Huddersfield Town. Following the game, the club released an official statement saying McDermott had not been dismissed and remained first team manager, and he returned to take first team training on 3 February. On 7 February, it was reported that Cellino had agreed a deal to buy the club subject to approval from the Football League. On 24 March, it was announced that the takeover deal had been vetoed unanimously by the Football League after Cellino was found guilty by Italian courts of failing to pay import duty on a yacht, though the takeover was completed after Cellino successfully appealed this decision. On 7 May, former managing director David Haigh's company, Sport Capital, issued a winding-up petition for a fee owed of around £1m on 7 May. On 10 June, the winding-up petition issued to Leeds by Sport Capital was adjourned but the case remained live and the club were ordered to pay back £958,000 by 23 June. The winding-up petition was dismissed by the High Court when heard on 23 June, resulting in the club's bank account being unfrozen.

Pre-season events Following the end of the 2013–14 season, in which Leeds eventually finished 15th, manager Brian McDermott left the club by mutual consent. Former Forest Green Rovers manager Dave Hockaday was appointed head as coach of Leeds United on 19 June, with Junior Lewis appointed as his assistant coach. Ahead of the summer transfer window, manager Hockaday claimed that Leeds' squad was too big, claiming "there's excess baggage in every department" that needed to be trimmed, and that he wanted a "tight-knit squad". On 16 May 2014, it was announced that first-team players Jamie Ashdown, Michael Brown, El Hadji Diouf, Adam Drury, Paul Green, Danny Pugh and Luke Varney would not be offered new contracts by the club and were released, as were academy players Simon Lenighan, Nathan Turner, Lewis Turner, Richard Bryan, Smith Tiesse and Gboly Ariyibi. In addition, defenders Lee Peltier and Marius Žaliūkas both had their contracts terminated in order to sign for Huddersfield Town and Rangers respectively. Forward Ross McCormack, who was the top goalscorer in the 2013–14 Football League Championship with 28 goals, transferred to Fulham for an undisclosed fee, reported to be £11 million by BBC Sport. He had submitted a transfer request on 20 June and did not travel for the club's pre-season training camp in Italy, and though owner Cellino initially claimed he was not for sale, he said he was "disrespected" by McCormack and he "had no choice" but to sell him, whilst McCormack claimed he was "hung out to dry" over the transfer. Leeds were later charged with misconduct by The Football Association over the transfer for breaching the FA's football agent regulations over an illegal payment to McCormack's agent Derek Day, and Cellino was banned for 18 months in December 2016.

Cameron Stewart, who had joined the club on an emergency loan from Hull City in January 2013, had agreed to sign permanently for the club at the end of his Hull contract, but this transfer was cancelled by Leeds and he signed for Ipswich Town instead. Stewart's contract agreement with Leeds was not accepted by the Football League as it was signed by former managing director David Haigh, who had been removed from the club's "authorised signautures" list after a dispute with new owner Cellino, and Cellino claimed the contract was invalid rather than re-signing it himself. Stewart later lodged a compensation claim against Leeds United, which he won in May 2015, with Leeds ordered to pay Stewart around £800,000. This compensation was unpaid until the club was threatened with a transfer embargo in July 2015.

Hockaday confirmed on 26 June that the club was currently under a transfer embargo, though the embargo was lifted shortly after as Leeds signed goalkeepers Stuart Taylor (on a free transfer) and Marco Silvestri (for an undisclosed fee from AC ChievoVerona), as the first two transfers of the summer transfer window. Midfielder Tommaso Bianchi and forward Souleymane Doukara both joined from Italian clubs on 12 July; Bianchi was signed for an undisclosed fee from Sassuolo whilst Doukara joined from Catania on a season-long loan, though Doukara was later transferred permanently for an undisclosed fee on 1 September. On 19 July 2014, Swiss defender Gaetano Berardi joined for an undisclosed fee from UC Sampdoria, and signed a two-year contract with the club. Young Slovenian midfielder Žan Benedičič joined on a season-long loan on 4 August, and on the following day, striker Nicky Ajose joined from Peterborough United for an undisclosed fee.

Pre-season friendlies Pre season games against Guiseley and Chesterfield were confirmed by the club on 27 June.A pre season game against Glenavon was confirmed by the club on 29 June. The Glevavon game forms part of the contract that saw Robbie McDaid sign for United in March. The club also confirmed a Leeds XI will face Corby Town.Two pre season games in Italy were confirmed on 2 July, against local team FC Gherdëina and Romanian team FC Viitorul Constanța. However, the Viitorul Constanța was called off after the Romanian side failed to show up.A pre season game against Swindon Town was confirmed on 7 July.A pre season game against Mansfield Town was confirmed on 8 July, whilst the Glenavon game was confirmed as being for a Leeds XI.The club confirmed a home game against Dundee United will complete the team's pre season schedule on 9 July.

Review

July 1 July: Transfer embargo is lifted days after club's bank account is unfrozen

August 28 August: David Hockaday and Junior Lewis's contract as head coach and assistant coach are terminated with immediate effect, with Neil Redfearn taking over as caretaker head coach.

September 23 September: Darko Milanič announced as the new head coach after signing a two-year contract, with Neil Redfearn returning to his role of Academy manager and head of coaching, and Novica Nikčević joining as assistant coach. 26 September: Consultant Graham Bean is sacked over a fixture dispute, relating to the rearrangement of the home fixture vs. Reading.

October 25 October: The club part company with Darko Milanič, after failing to win in six games.

November 1 November: Academy manager Neil Redfearn is appointed as head coach on a one-year rolling contract, with the contract including the option to return to the club's Academy. 7 November: Leeds United have been served with a winding-up petition by law firm Ford & Warren Solicitors over unpaid fees of £150,000, that date back to when Ken Bates owned the club. The club issued a statement confirming the receiving of the winding-up petition. However, due to the illegal the winding-up order to the media within seven days of its service, the club's lawyers demanded that the petition be immediately withdrawn, and a full apology made else the club will ask the court to dismiss the petition on Monday morning. 12 November: The winding up petition presented by Melvyn Levi is dismissed on agreed terms. 27 November: Companies House confirm that David Haigh and Salah Nooruddin have resigned from Leeds United’s board – several months after the two men actually quit as directors. Salem Patel remains as a director and GFH revealed that Jinesh Patel, the CEO of Dubai-based GFH Capital, joined him on the Leeds’ board earlier this year.

December 1 December: The Football League disqualify Massimo Cellino from being a director of Leeds United Football Club until 18 March 2015. 4 December: Massimo Cellino and GFH Capital signed an agreement on 1 December to inject up to a further £20m of equity capital into the club.