Cardiff City will be in the High Court on Wednesday to face their second winding-up order over an unpaid debt to Her Majesty's Revenue and Customs.The Bluebirds have been in discussions with HMRC over a reported £2.7m tax bill in an effort to reach an agreement so Wednesday's action could be dropped.
But the Championship club, served with the winding-up petition on 23 December, have yet to agree a compromise.
Club chairman Peter Ridsdale will be in court hoping to reach a deal with HMRC.
Earlier this month Cardiff raised a reported £1.5m by selling two plots of undeveloped land around its new stadium after the local council gave permission.
Ridsdale is expected to put forward a proposed deal with HMRC in court, with a substantial part of the money owed being paid immediately and the rest of the debt to be paid in instalments.
The Championship play-off hopefuls, however, could face administration and a 10-point deduction should the winding-up order be made.
Chairman Peter Ridsdale will represent Cardiff City in the High CourtAlso on Wednesday's companies court list for Wednesday is Cardiff's 2008 FA Cup final opponents Portsmouth - who beat the Bluebirds 1-0 at Wembley - as the Premier League club has a £7.5m VAT bill.
League One club Southend United are also listed in Wednesday's winding-up list, with HMRC adopting a tougher stance on football clubs.
Cardiff - case number 22182 - and the two other football clubs are listed to appear at the High Court after 1130 GMT.
Ridsdale claimed at the start of last month: "We have every confidence that all monies owing to HMRC will have been repaid by the end of January.
"HMRC booked a back stop date of 10 February 2010 to go back to court if, for any reason, we had not been able to fulfil our obligations to pay by the end of January."
But Cardiff, who reached a settlement over their long-standing £15m debt with former owner Sam Hammam's Langston Corporation in December, have failed to avoid further court proceedings.
Bluebirds fans protested at chairman Peter Ridsdale's handling of finances after Saturday's game as the cash-strapped club face a winding-up order.
Around 200 Cardiff fans protested against Ridsdale's handing of club affairs outside the Cardiff City Stadium following their 2-1 victory over Doncaster Rovers last month.
Ridsdale was forced to apologise to fans after funds - an estimated £3m - raised from advance season tickets sales, which the chairman initially promised would be spent on buying new players in the January transfer window, will now be used to settle debts.
Cardiff are effectively up for sale and former Leeds United chairman Ridsdale had promised "new investment" into the club "soon."
Malaysian businessman Datuk Chan Tien Ghee's arrival onto the club's board on the day they saw off their first winding up order at the High Court gave hope of fresh investment.
Cardiff have been in discussions with Malaysian and American investors over a possible £40m takeover while Guernsey-based property developer Ben Steele had also been in talks with Ridsdale.
The club moved from their old Ninian Park home to their new £50m 26,500-capacity Cardiff City Stadium last summer which the club hoped would double the club's turnover to approximately £16m to £18m.
Source: BBC Sport