Dundee Football Club have been deducted 25 points by the Scottish Football League for going into administration.
The First Division outfit have also been banned from signing any new players until they come out of the administration process.
The SFL board said in a statement: "We are of the opinion that lessons are not being learned.
"Clubs have to realise that they can't treat their HMRC tax obligations as something akin to a credit card."
The deduction will leave the Dark Blues second-bottom of the First Division on minus 11 points, 20 behind the nearest team Morton, with 25 league games left to play.
As well as posing a major task for the team to save their Division One status, the position - and possible relegation - could put off any potential investors.
The SFL board added in their statement added that if the Tayside club are still in administration by 31 March 2011, they will "reconsider the matter and deal with the club as it sees fit."
Administrator Bryan 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 £365,000.
In an effort to streamline their operational costs, the management team and nine players were made redundant.
Dundee's benefactor Calum Melville had put in around £1.3m in to the club since he became involved March 2009.
He resigned from the Dens Park board in September, but lodged £200,000 as part-payment for the outstanding tax arrears.
Dundee also went into a administration in 2003 when they were in the Scottish Premier League.