The owners of Blackpool Football Club have been told by a High Court judge to "concentrate" their minds on paying the £25 million still owing to minority shareholder Valeri Belokon.
Owen Oyston and his son Karl were ordered to hand over £31.27 million to the Latvian millionaire after losing a court battle in London in November.
The Oystons were ordered to buy out Belokon's shares after operating an "illegitimate stripping" of the club following its promotion to the Premier League in 2010.
They met a December 4 deadline to pay the first £10 million and now they have to comply with a judge's ruling that they pay the remainder, including interest, in staged payments.
Describing their evidence as "woeful", Mr Justice Marcus Smith ordered the Oystons to pay another £10 million by 4pm on January 31; and two lots of £7.5 million by March 30 and May 31.
He also ruled that they had breached the terms of an injunction freezing their assets by negotiating a £5 million loan on two properties to put towards December's payment without prior consent of Mr Belokon. But the judge retrospectively approved that deal.
Mr Justice Smith said: "The evidence has been unsatisfactory indeed. I can have very little faith in the cash flow projections they put together.
"I have no clear understanding of the future financial needs of the Oyston Group.
"I have very little understanding of the assets within the group save for repeated assurances that they are both liquid and valued beyond the extent of the sums due."
He added: "Indeed I cannot be sure even about the insolvency of the Oyston Group.
"I have been told about valuation of the assets and about cash flows and about credit obligations and I am told assets exceed debts but the material I have I am sorry to say is woefully inadequate."
The judge said he had to ensure that paying was a priority. The deadline of 4 December had proved effective.
"It seems to me a stringent plan of payment is necessary in order to concentrate the mind," he said.
The Oystons are currently seeking leave to appeal the original court decision.
The lawyer acting for the Oystons claimed there had been "substantial interest" in the football club, which was put up for sale last month.
Read tomorrow's The Gazette for more.