Sky Bet Championship club Bolton have confirmed they have been served with a winding-up petition from HM Revenue and Customs over an unpaid tax bill.
Wanderers' alarming financial crisis has deteriorated rapidly over the past few weeks after it was revealed they had failed to pay their players for November, and now HMRC has rejected requests from them to be given more time to conclude a sale.
Bolton had hoped they could conclude a takeover this week after drafting in financial advisor Trevor Birch to help long-time owner Eddie Davies, who is willing to wipe out ?185million of loans owed to him, sell the club.
However, with discussions still ongoing, HMRC has now acted to call in unpaid PAYE and VAT for the month of November.
It raises the possibility of administration for Neil Lennon's bottom-of-the-table side, who would have their entire total wiped out if they were to incur the 12-point deduction.
A statement on the club's official website read: "Bolton Wanderers can confirm that the club has now received a winding-up petition from HMRC in respect of unpaid PAYE and VAT for the month of November.
"Despite requests from the club to HMRC to give it further time to either conclude a sale or raise additional funds, HMRC has proceeded with due process and duly served a petition."
Birch added: "Quite clearly the club remains in a critical financial position.
"We will continue to try and finalise a sale or alternatively raise some short-term funds needed to give the club a breathing space and time in which to consider its options."