League Two club Northampton Town have been issued with a winding-up petition by HM Revenue and Customs (HMRC).
The petition relates to money outstanding following delays to a takeover, after an Indian consortium pulled out of purchasing the club.
This is separate to a £10.25m loan from the local council which the Cobblers have until Thursday to repay.
Northampton chairman David Cardoza has said he "fully expects the matter to be resolved by the end of next week".
The news comes after the London-based consortium, who have been known to be interested in the club since June, pulled out of the deal on Monday because of "a number of complications surrounding the proposed acquisition".
Cardoza said that the club have moved on to speak with other interested parties, who know of the HMRC discussions, and there would be "definite news very soon".
The BBC understands Northampton Town owes HMRC a "five-figure sum".
In a statement, a HMRC spokesperson said: "HMRC does not in general comment on the tax affairs of individual businesses, but our aim is to efficiently collect the debts due and to prevent things deteriorating further.
"We only initiate winding-up action where we believe this is the best way to protect both the interests of other taxpayers and creditors."
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Meanwhile, the 21-day deadline to repay a loan from Northampton Borough Council is also on Thursday.
The original loan from the council was given to the club for the re-development of Sixfields Stadium, and was to be used to build the new East Stand, along with a hotel and conference centre - none of which have been completed.
One option the club is looking at to repay the council loan is to sell off land behind the East Stand, with at least two developers said to be interested.
"We are putting proposals to Northampton Borough Council regarding the repayment of the loan which we hope will prove satisfactory to them and that process is ongoing as we speak," said Cardoza.
"I fully appreciate that, off the pitch, there only seems to be bad news for supporters at the moment but we are working towards, and we believe we are close to, a conclusion on all matters that tidies up all of the issues surrounding the club and allows it to move forward to a much brighter future."
A Northampton Borough Council spokesman said: "Following this morning's announcement, we are contacting HMRC and are requesting an urgent meeting with them.
"Our priority now is to understand what is happening at the football club and the impact this action will have. When we have the facts on this, we will consult our legal advisors about the appropriate steps regarding our loan to the club."