Portsmouth have struggled in the Premier League this season
Portsmouth FC has failed to block a winding-up petition from HM Revenue & Customs at the High Court.
HMRC had applied for the petition on 23 December but the club argued the VAT part of its tax bill was too high.
The High Court judge dismissed Portsmouth's claim and the hearing is expected to go ahead on 10 February.
But he said the issues involved in the case were "difficult" and granted the football club permission to appeal against his ruling.
Court of Appeal
"At the High Court today Mr Justice Newey dismissed an application from Portsmouth City Football Club Limited for a winding-up petition to be struck out," a spokesperson for the Judicial Communications Office said.
HMRC said it welcomed the High Court's decision.
"We now expect that, subject to any appeal, the petition will in due course be heard by the High Court in the usual way," a spokesperson said.
If it goes against them, it would push Portsmouth a step closer to administration.
However, a statement from Portsmouth said the judge "considered any appeal to the Court of Appeal would have a 'real chance of success'".
If it were to succeed, the club said, "this would result in the judge's ruling being reversed and HMRC's petition being struck out, without the petition proceeding to the final hearing".
Portsmouth now has seven days to lodge at appeal.
Portsmouth has found itself in financial difficulties this season - failing to pay its players on time on three separate occasions.
Last week, the Premier League diverted £7m in television revenue payments to other clubs which were still owed transfer fees by Pompey.
However, Portsmouth executive director Mark Jacob said the club had directed the Premier League to pay only £5m, and so it was in fact owed £2m.
The Premier League has also banned the club from operating in the transfer market.
The Fratton Park club won the FA Cup in 2008, but since the departure of manager Harry Redknapp, its fortunes on the pitch have declined.
The club is currently bottom of the Premier League.
If the club were to go into administration, it would face an automatic nine-point deduction.