Macclesfield Town Football Club has been wound up in the High Court over debts totalling more than £500,000.
Judge Sebastian Prentis made a winding-up order during a hearing in the Insolvency and Companies Court after being told £190,000 was owed in tax.
In addition, a solicitor for John Askey said the National League club's ex-manager was owed £173,000, while a financial lender was owed the same sum.
The club's owner Amar Alkadhi had asked for a further eight-week adjournment.
The decision to wind up the club comes just over a month after Macclesfield were relegated from the English Football League (EFL) at the end of a tumultuous 2019-20 season on and off the pitch.
Players went on strike in November after failing to be paid, which resulted in the club fielding youth players in their FA Cup defeat by Kingstonian, while the Silkmen were deducted points on three separate occasions for issues relating to payment of salaries and failure to fulfil League Two fixtures against Plymouth and Crewe.
Alkadhi stepped down as chairman in August, just before the EFL won an appeal against what they saw as a lenient points deduction.
The stronger punishment imposed by an independent panel resulted in their relegation to the National League and a reprieve for Stevenage, who had finished bottom of the fourth-tier table when the season was curtailed because of the coronavirus pandemic.
'Ample opportunity' to pay creditors, says judge
The winding-up petition, which had been adjourned for a 12th time last week, began in January 2019 and was scheduled to be heard again on Wednesday after Alkadhi claimed that a sale to Robert Benwell was at an advanced stage.
Benwell, who previously tried to buy Bury, was not mentioned in court on Wednesday by Alkadhi's lawyer, who asked for a further eight weeks to allow a sale to go through.
The judge later said that a business plan from Benwell had not been put forward to the court, however.
The court was told that Alkadhi understood the amount due to creditors was actually just £4,000, had made a late offer to pay an initial £20,000 of the debt owed to HM Revenue & Customs and had made available a screenshot of a bank statement with £1.1m of funds to show that creditors could be paid.
However, Judge Prentis said he would grant a compulsory order, saying "nothing gives me comfort that the club can pay its debts in a reasonable period" and that there had been "ample opportunity" for Alkadhi to pay off creditors.
He went on to say that he had not been told by Alkadhi where the £1.1m had come from or why outstanding debts had not already been paid.
146 years of history
Having initially been founded as Macclesfield in 1874, the club were reformed in their current guise - Macclesfield Town FC - in 1946 following the end of World War Two.
A club with a rich history in non-league football, twice winning the FA Trophy, they were promoted to the Football League for the first time in 1997.
They spent 15 years in the EFL, even briefly playing in the third tier, before being relegated back into the Conference in 2012.
The Silkmen earned promotion back into League Two in 2018, but their most recent stay in the EFL was to prove short lived after a host of financial problems which eventually culminated in their relegation in August.