Former Wimbledon champion Boris Becker has been declared bankrupt by a British court on 21 June, after failing to pay off a long-standing debt.
The tennis star's lawyers called for "a real last chance" for him to settle his debts which were outstanding since 2015.
Judge Miss Registrar Christine Derrett said Becker was "not a sophisticated individual when it comes to finances" and she felt that there was little evidence that he might recover his "substantial debt" soon.
Declining to adjourn the case for a further 28 days she said Becker was "a man with his head in the sand."
"It is not often the case that a professional person has a judgment outstanding against them since October 2015," the judge said. "This is a historic debt."
The bankruptcy application was made by private bankers Arbuthnot Latham & Co following a previous judgment ordering Mr Becker to pay a debt owed to them since 2015 according to Sky News.
The 49-year-old's lawyers argued there was evidence to show the debts could be repaid by remortgaging a property in Majorca, which was expected to raise €6m (£5.27m).
In a statement, Becker said he was "surprised and disappointed" that Arbuthnot Latham had chosen to bring the proceedings against him.
"This order relates to one disputed loan which I was due to repay in full in one month's time," he said.
"It is disappointing that my request for today's hearing to be postponed until this time was refused. My earnings are well publicised and it is clear that I have the means to repay this debt. The value of the asset in question far exceeds the debt owed to Arbuthnot Latham."
His lawyer, John Briggs, had argued there was sufficient evidence to show that Becker would be able to pay the debt through a refinancing arrangement, involving remortgaging a property in Mallorca, which was expected to raise €6m ($6.7m). Briggs said it was expected the deal would be approved by a Spanish bank in about one month.
The three times Wimbledon champion has served as a sports pundit since retiring and also coached former world number one Novak Djokovic for three years from 2013.