Championship strugglers Bolton Wanderers have been served with a winding-up petition from Her Majesty's Revenue and Customs (HMRC) over unpaid PAYE and VAT in November.
Bolton have racked up huge debts since falling out of the Premier League in 2012 and announced a deficit of £172.9million in April of this year.
The Lancashire club's crisis deepened when players failed to receive wages on time for November.
Bolton have now fallen foul of HMRC, with a club statement reading: "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."
Trevor Birch, an advisor to the board and owner at Bolton, 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."
Birch was appointed as an advisor to help orchestrate a takeover of the club.
Bolton's problems off the pitch have been mirrored on it, with Neil Lennon's side bottom of the table having taken just 12 points from 19 matches this season.
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