Rangers face more financial pressures after failing to secure permission to appeal against the imposition of a £250,000 fine for undisclosed payments to players.
Rangers are fighting the Scottish Professional Football League's (SPFL) attempts to recover the fine, which was handed down over the oldco club's failure to disclose many untaxed payments to players throughout the first decade of this century.
The club announced they had lost an appeal with a Scottish Football Association (SFA) judicial panel and would take the matter to arbitration, but it is understood that their fight did not get past a preliminary hearing.
The defeat could add to the financial problems at Ibrox as the SPFL is prepared to withhold prize money and broadcast income payments to the club, who had previously admitted they were set to run out of money before the end of January.
They now have two options - to take the case to the Court of Arbitration for Sport or to persuade the SPFL to use the SFA's arbitration procedures to settle the dispute.
Rangers announced last month they were fighting attempts to enforce the punishment but the SPFL insisted that the newco club had signed an agreement accepting liability for such sums, a position they say was later accepted by Ibrox board members in relation to the £250,000 fine.
A club statement on Wednesday read: "Further to the announcement on 17 December 2014, Rangers Football Club Limited lost the appeal with the judicial panel of the Scottish FA on 13 January 2015 in respect of the EBT Commission fine of £250,000 levied on RFC 2012 PLC (previously The Rangers Football Club plc) (in liquidation). The club will now take the matter to arbitration."
However, the case was not heard by an appeal tribunal but a preliminary panel that ruled Rangers did not have the right to challenge the SPFL's attempts to recoup the money because they were not a "determination of a recognised football body" but rather an interpretation of an agreement between two parties.
Rangers will thus have to prove they did not accept liability for such fines when they signed the five-way agreement, which paved the way for them to transfer the oldco club's SFA membership and join the Scottish Football League in July 2012.
The case could be settled through the SFA's arbitration process. The procedure would see both sides appoint an arbitrator from an SFA list or alternatively one representative each with a third arbitrator, a lawyer, acting as chairman.
If the SPFL does not agree to this process, or Rangers prefer another route, then the club could go to the Swiss-based Court of Arbitration for Sport.
In a statement on December 17, the SPFL said Rangers had signed an agreement "under which they would be liable for sums such as this".
The statement added: "The chairman of Rangers FC, David Somers, and on one occasion the club's then chief executive Graham Wallace, engaged in individual discussions with the majority of current SPFL board members several months ago acknowledging the liability and suggesting ways of paying the sums due.
"Following such discussions, it was only when no sums actually arrived from Rangers FC that the SPFL board decided to offset this liability against future sums payable to the club."
The undisclosed payments related to the club's tax-avoiding Employee Benefits Trust scheme and totalled £9million in one season alone.
Former owner Murray International Holdings has largely won two court cases against Her Majesty's Revenue and Customs over the scheme, with another one planned, but the commission focused on the club's use of undisclosed side letters to players rather than the legality of the payments.
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