Rangers are facing a tax demand of £49m including penalties levied by HM Revenue and Customs if they lose a tax tribunal.
Rangers are challenging a bill for £35m in back taxes, as well as £14m in penalties, over their use of an Employee Benefit Trust to pay players between 2001 and 2010.
The Tribunal is expected to last five days and should the Ibrox club lose owner, Craig Whyte, has conceded that administration could follow.
John Cairns, convenor of the taxation committee for the Institute of Chartered Accountants of Scotland concluded
“If the club loses, probably the most likely scenario is going into administration to get rid of this enormous debt.
“By the sound of it there’s a chance of HMRC pursuing this quite vigorously because we have a high profile tax payer here.
The outlook for Scotish football could never be the same again if the taxman is successful.