Scottish Premier League champions Rangers have appointed Duff and Phelps as administrators and, as a result, have been deducted ten points.
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The penalty all but hands the title to arch-rivals Celtic who, prior to any deduction, were four points clear at the top of the table.
On Monday, Rangers began preparations to go into administration and said a final decision would be taken in ten working days.
But their hand was forced following a short legal battle with Her Majesty's Revenue & Customs and the Edinburgh Court of Session gave the club until 15.30 GMT on Tuesday to appointment their own administrators, or the tax authority would do it for them.
Rangers appointed their preferred administrator, Duff & Phelps, with around 45 minutes to spare and they later confirmed HMRC had taken action over an unpaid tax bill of £9 million - accrued since Craig Whyte's takeover.
They said in a statement: "The appointment follows a petition for administration presented to the Court of Session in Edinburgh today by HMRC following the non-payment of circa £9 million PAYE and VAT following the takeover of the club in May 2011.''
The Scottish champions' perilous financial state is underlined by the fact that they are still awaiting the verdict of a tax tribunal which Whyte claims could cost them £75 million.
The club's former chairman Sir David Murray, who many blame for Rangers' financial difficulties, released a statement through his firm Murray International Holdings expressing his huge disappointment at the situation.
He also confirmed that, contrary to speculation, there was no legal mechanism in place for him to take over the club again. "The timing of the appointment of administrators is especially surprising given two facts," Murray said.
"Firstly, there has been no decision, and there is no present indication as to the timing of a decision, from the first-tier tax tribunal concerning the potential claim from HMRC of £36.5 million excluding interest and penalties.
"Secondly, legal opinion on the strength of the club's case remains favourable. Murray International Holdings is saddened by the appointment of administrators. It recognises the tax-tribunal proceedings have stemmed from arrangements put in place during the time of its ownership.
"However, these arrangements and details of the proceedings were fully disclosed by the club to (Whyte's company) Wavetower and Craig Whyte in the due diligence process."
It is understood that HMRC's court action this week has nothing to do with the so-called 'big tax case' surrounding employee benefit trusts, which was heard at a tribunal last month, but on unpaid bills such as VAT and PAYE from the current financial year.
An HMRC statement today read: "We can't discuss specific cases for legal reasons but tax that has been deducted at source from the wages of players and support staff such as ground keepers and physios, must be paid over to HMRC. Any business that fails to meet that basic legal requirement puts the survival of the business at risk.''
Rangers' next SPL game, against Kilmarnock at Ibrox on Saturday, will go ahead after Strathclyde Police received assurances from the administrators they would be paid for policing the event."
The points penalty means Rangers fall 14 points behind SPL leaders Celtic but are still nine above nearest challengers Motherwell, who have a game in hand.
Rangers also face a race to prove to the Scottish Football Association that their finances are in shape before March 31 or face expulsion from Europe next season.
Although there is no specific ban on clubs in administration playing in Europe, it would be very difficult for such a club to meet the other financial criteria needed for a licence.
The SFA's chief executive Stewart Regan called for lessons to be learned from Rangers' "dire situation''. In a statement, he said: "This is a profoundly sad chapter in the history of Scottish football and we should not underestimate the potential ramifications for the image of the game as a whole.
"At a time when there is an appetite and momentum for radical change in Scottish football, it is important that we learn lessons from this dire situation and work together to provide a platform for clubs to thrive and prosper within their means.''