Portsmouth have been dealt another blow after their application to have a winding up petition from Her Majesty's Revenue and Customs struck out was dismissed by a High Court judge.
The club have argued that the VAT portion of its massive tax bill is too high by £7.5 million, but failed to convince Mr Justice Newey.
A spokesperson for the Judicial Communications Office said: ''At the High Court today (Tuesday) Mr Justice Newey dismissed an application from Portsmouth City (sic) Football Club Limited for a winding up petition to be struck out. A further hearing to consider HMRC's winding up petition will take place in due course.''
That hearing is now expected on February 10, and the outcome could send Portsmouth a step closer to being the first Premier League club to drop into administration.
Tuesday's decision is the latest blow for Pompey's owner Ali Al-Faraj, who has been battling huge debts since the day he took over.
But an argument with the tax man is by far the most serious, particularly given HMRC's increased willingness to serve football clubs with winding-up orders since losing their status as a preferred creditor of those in administration.
Portsmouth have been fighting financial fires on several fronts this season. They have three times failed to pay their players on time, and only last week saw the Premier League divert £7 million in television revenue payments to other clubs who were still owed transfer fees by Pompey.
The Premier League made that move after meeting with club officials but coming away unconvinced that they were in any position to pay their debts on a series of deals, many involving players such as Glen Johnson and Lassana Diarra who have since been sold on.
That has prompted the club to threaten arbitration proceedings against the Premier League, who have imposed a transfer embargo on the club.