The Supreme Court has ruled in favour of Her Majesty's Revenue and Customs in its fight with Rangers over the club's use of Employee Benefit Trusts.
The tax authority opened its investigation into Rangers in 2010 after about £50m worth of payments were made to dozens of employees through EBTs from 2001, and the case continued after the Glasgow-based club was liquidated over an unrelated tax debt in 2012.
The club contended that these should be classified as loans, but HMRC insisted that they were taxable earnings.
After suffering two tax tribunal defeats to the Murray Group, the former majority shareholder of Rangers which administered the EBT scheme, the Court of Session found in favour of HMRC after an appeal in Edinburgh in November 2015.
On Wednesday, Lord Hodge announced in court that five Supreme Court judges had unanimously dismissed an appeal by the liquidators of RFC2012, the company formerly known as Rangers Football Club before its financial collapse in 2012.
The result will mean the creditors of RFC2012 will receive less money from the pot collected by liquidators BDO, as HMRC will now be owed even more.
The court's decision is not expected to have any material or financial impact on Rangers now as the club is owned by a different company but it could have broader implications for British football clubs.