Former Wimbledon champion Boris Becker, convicted of tax evasion last year, returned to court on Thursday seeking to defend himself in a 1.5 million euro ($1.69 million) lawsuit.
Becker faces a claim from the administrator of insolvent Internet portal Sportgate.
The administrator claims Becker, who was a majority stakeholder in the company, had promised to pay it 1.5 million euros to cover the firm's losses. Becker denies the charge.
The website was supposed to be the portal for the German Sports Federation but the company filed for insolvency in 2001.
Judge Stefan Bischoff told the court on Thursday he believed it would be difficult for the administrator to prove its case and queried how the figure of 1.5 million euros plus interest had been reached.
Thursday's hearing represented a final bid to settle the dispute without a lengthy court case. Becker's lawyers offered 50,000 euros but the administrator said that was not enough.
Bischoff suggested a sum of about 150,000 to 300,000 euros, which the administrator also rejected.
The judge suspended the case until December.
Becker said he had signed a declaration agreeing to cover Sportgate's losses of up to 1.5 million euros after meetings in Paris and Washington D.C. with the head of Pixelpark, a darling of the new media revolution until the dotcom crash.
However, Becker had not provided a guarantee, leaving competing lawyers to argue on Thursday over whether the declaration was legally binding.
The three-times Wimbledon champion has run into considerable trouble since retiring from tennis in 1999, including a costly divorce, an admission he fathered a child with a Russian model and a string of failed business ventures.
Last October, Becker received a two year suspended jail sentence and a 500,000 euro fine after being convicted of tax evasion for claiming residence in Monaco while actually staying in Munich between 1991 and 1993.
He has also faced demands for unpaid business taxes from the city of Munich. Becker's lawyer said last month he expected to be able to reach a settlement.