RANGERS were last night warned they will be unable to agree a compromise with Mike Ashley over their controversial retail deal with Sports Direct until they repay the £5 million he loaned them in January.

Ashley, the enigmatic billionaire owner of Newcastle United, has launched a third legal challenge, over an unpaid SFA fine totalling just £1,000, which relates to his interest in the Ibrox club.

He is already involved in actions against Dave King, the Rangers chairman and major shareholder, for allegedly breaching the terms of an injunction, and the SFA for passing King, who has tax convictions in South Africa, as a fit and proper person.

The new Rangers board has been unable to renegotiate the terms of an agreement with Sports Direct - which was almost certainly one of the “onerous contracts” former chief executive Graham Wallace mentioned in the business review he published last year – since taking control in March.

Supporters are refusing to buy replica strips and official merchandise in large numbers amid speculation the club only receives 50p from every £10 which they spend at the nationwide chain of sports good stores.

The increasingly acrimonious stand-off is concerning given that Rangers posted a £7.5 million loss in the last financial year and revealed they will need loans of £2.5 million – which will be forthcoming from King as well as George Letham, Douglas Park and George Taylor – to stay afloat until the end of the season.

Senior club officials expect the financial results to be far more favourable next season as a result of increased season ticket sales and improve attendances at home games during the 2015/16 campaign.

But King has previously admitted Rangers, who are five points clear at the head of the Championship table and hopeful of winning promotion to the top flight this season under new manager Mark Warburton, will be unable to challenge Celtic for the Premiership unless the contract can be changed.

But Nicla Di Palma, a retail analyst at major investment management firm Brewin Dolphin, believes the only prospect of reaching a truce with the mercurial businessman hinges on returning the £5 million he handed Rangers earlier this year in full.

“Mike Ashley doesn’t strike me as somebody who does things from the goodness of his own heart,” said Di Palma. “There has to be money in it for him. He is not going to back down very easily from the current agreement if it isn’t in his best interest to do so.”

The Englishman received security over the Albion Car Park, Edmiston House, Murray Park and the registered trademarks as well as receiving a controlling stake in Rangers Retail Ltd after agreeing to a £10 million loan with the previous regime.

Derek Llambias, the former Newcastle United chief executive, and Barry Leach, the former Sports Direct Head of Brands, were serving on the board as chief executive and finance director respectively at the time the deal was agreed.

The money, only £5 million of which has been drawn down, was interest free and there was no time limit put on its repayment so, given the financial problems they have inherited, the new hierarchy have decided not to reimburse him at this time.

Di Palma said: “If he has complete control, either the club repays the money, which doesn’t sound easy since they don’t have any money, or they follow the current agreement to the letter. The situation is very difficult for the club.

“Why would he back down from this contract if it’s in his own interest and if it’s what he agreed? I would be very surprised Mike Ashley signed something that wasn’t bulletproof. If they can’t repay the £5 million it’s going to be tough times for Rangers.”

The prospect of tens of thousands of supporters buying jerseys and other products - something which King has vowed would happen if a new agreement which was more beneficial to Rangers could be struck – should appeal to a shrewd businessman like Ashley.

However, Di Palma, who analyses the performance of Sports Direct and his other business interests, believes he has responded to his loss of influence at Rangers by going on the offensive against those responsible.

“There is certainly potential for renegotiating the deal,” she said. “You would think he would agree to a better profit split if he could increase revenue and increase sales.

"But nobody can read Mike Ashley’s mind or say with any confidence what his objective is. He has an irregular way of running his companies.

“It is fair to say he protects his interests very aggressively. I don’t think he is taking what has happened at the club this year sitting down. He has three legal challenges ongoing. He wants his money back. That is his response. He is not standing still.

“If the club doesn’t have the money then obviously they can’t repay the money. So how are they going to repay the £5 million? A bank will not loan money to a club which is losing money. It is a very complicated situation. I don’t see how they can get out of it.

“But the question in all of this really is: ‘Why did previous management sign the agreement if it wasn’t good for the club?’ I have no idea.”