He is suing his former employer ARN, owner of KIIS and Gold radio stations, over claims his lucrative contract was invalidly terminated in March because there was no serious misconduct.
The top-rating provocateur and one-time TV judge is pushing to return to the air and earn the estimated $85 million left on his contract as soon as possible.
"Mr Sandilands' continued absence from broadcast radio and his audience of at least a million listeners each week ... will irreparably harm (him)," his lawyer Kevin Lynch wrote in court documents.
"Each day of continued absence from air compounds the harm in a manner that is irreversible and incapable of adequate assessment in monetary terms."
But lawyers for his radio bosses poured cold water on his claims during the first mention of the matter in the Federal Court on Friday.
"We don't accept the central premise that Mr Sandilands' goodwill and notoriety is dramatically wasting away for every day he's not on air," ARN's barrister Tom Blackburn SC said.
The possibility of Sandilands receiving the desired orders that he return to the air was "vanishingly small", he told the court.
"This is, in substance, a claim for a debt," Mr Blackburn said.
"He wants his $10 million a year for the next eight or nine years."
ARN denies Sandilands's claims that it invalidly tore up his contract, claiming he committed serious misconduct by causing a rift with co-host Jackie "Jackie O" Henderson.
It said Henderson gave notice she could no longer work with her co-host in February, triggering an early March decision to terminate the remainder of her 10-year, $100 million agreement.
The company was considering whether to make a cross-claim against the radio host for his prior conduct towards Henderson, Mr Blackburn said.
ARN had hired the shock jock for his robust conduct and could not now consider it misconduct, his barrister told the court.
It had been agreed Sandilands would be immune if the radio company did not censor content before it went on air, Scott Robertson SC said.
"This is not a case for a royal commission into Mr Sandilands and his radio career," he said.
Mr Robertson pushed for the matter to be expedited and set down for a three-day hearing, noting most of the dispute has been outlined in correspondence between lawyers.
"The battle lines have already been drawn," he said.
But Justice Angus Stewart held off on making the order, directing the parties to file further documents before the matter returns to court in April.
The end of the Kyle and Jackie O Show came after Sandilands in February slammed his broadcast partner for looking into former prince Andrew Mountbatten-Windsor's horoscope, accusing her of being "off with the fairies".
Sandilands was suspended on March 3 and issued a breach notice for serious misconduct, which he denies.
Outside court on Friday, Sandilands said he regretted his comments to Henderson while arguing it did not differ from his conduct over 25 years.
"We've had blow-ups before ... we just get over it, usually. So I think this has all turned into quite a circus," he said.
He said he was looking forward to getting back on the air so he could support his family and give his listeners what they wanted.
"I'm ready to go today," he said.
"Let's just hope we get back to work as soon as possible".
The Kyle and Jackie O Show was a consistent ratings juggernaut in Sydney but had failed to gain much traction in its expansion to Melbourne and Brisbane.
