Scottish Premier League side Hearts run the risk of going out of business after confirming Wednesday they had been served with a winding-up order regarding a tax bill of nearly 450,000 pounds ($719,000).
Her Majesty's Revenue and Customs (HMRC) submitted the petition in the Court of Session in Edinburgh.
In response, Scottish Cup holders Hearts said in a statement they were attempting to negotiate a payment plan with the tax authority.
This matter is unrelated to a £1.75million HMRC bill which the Edinburgh club are challenging at a tax tribunal.
Hearts said they were "endeavouring to agree a suitable payment plan with HMRC for the outstanding amount of Â£449,692.04".
A club spokesperson added: "We have guaranteed future revenues from forthcoming games and related broadcast income as well as additional guaranteed transfer income which will more than cover the outstanding amount stated in this petition.
"We would therefore be hopeful that HMRC will accept that winding up the club would be totally unnecessary.
"The club is revealing the petition as it wants to continue being transparent in all its dealings with supporters and potential investors."
Hearts launched a £1.79million share issue two weeks ago but the prospectus revealed another tax dispute.
HMRC has claimed unpaid tax liabilities in the region of £1.75 million relating to loan agreements for a number of players who joined Hearts from Lithuanian club Kaunas, who were then run by Vladimir Romanov, the Tynecastle club's majority shareholder since 2005.
Last year, Hearts had to pay a bill in the region of Â£500,000 to defeat a similar HMRC winding-up order, while others were served in 2009 and 2010.
The Jambos have had problems meeting wage bills during the past year and are currently under a Scottish Premier League transfer embargo following consecutive late monthly payments to some players and coaches.
This latest incident is bound to re-open the debate about the commercial viability of Scottish football which raged earlier this year when Glasgow giants Rangers, the country's most successful club, went into administration.
That started a process which led to Rangers being ejected from the SPL and demoted into the fourth-tier Third Division for this season because of financial irregularities, amid HMRC allegations of unpaid tax.