Dundee have been deducted 25 points by the Scottish Football League after entering administration.
The First Division outfit have also been banned from signing any new players until they exit administration.
The SFL board said in a statement: “We are of the opinion that lessons are not being learned.”
The club’s administrator Bryan Jackson said: “I shall be appealing this decision by the SFL as this is an outrageous punishment.”
The deduction will leave the club bottom of the First Division on minus 11 points, 20 behind the nearest team Morton, with 25 league games left to play.
Jackson was appointed in September to take control of the club’s business affairs after they failed to negotiate a deal over an outstanding tax bill of £420,000.
The SFL board added in their statement: “Clubs have to realise that they can’t treat their Her Majesty’s Revenue and Customs tax obligations as something akin to a credit card.”
They also said they will “reconsider the matter and deal with the club as it sees fit”, if the Tayside club are still in administration by 31 March 2011.