Shumsheer Singh Ghumman, 47, was refused bail in the Victorian Supreme Court on Wednesday after being charged with 35 offences.
It's alleged he stalked the professional chess player, aged in her 20s, between April 2024 and May 2026.
The woman obtained an intervention order against Ghumman in March 2025 but he allegedly continued to stalk her.
In refusing bail, Justice Amanda Fox said Ghumman had infiltrated the woman's life, finding out about her family, friends, addresses and even holiday plans.
"On the material I have, the offending is methodical and planned," the judge said.
During the bail application, police told the court Ghumman emailed officials in Qatar about the woman.
She was subsequently held in a jail cell after arriving at Doha International Airport, lead detective Senior Constable Ashley Hall said.
Ghumman is also alleged to have contacted the Icelandic Chess Federation and the woman was detained again.
The accused stalker also allegedly threatened to use artificial intelligence to surveil the woman and scrape her data from the dark web, Justice Fox noted.
He allegedly claimed to the woman that Claude - a reference to Anthropic's AI chatbot - would not get tired in his pursuit.
It's alleged Ghumman also tried to stop her from pursuing the criminal charges and also intimidated her parents and friends.
Ghumman was arrested at his Burnley cafe in Melbourne's east on May 1 and charged with 35 offences.
They included stalking, intimidation, attempting to pervert the course of justice and possessing a pair of nunchucks.
Ghumman denies the allegations and will take the case to trial, his barrister Dermot Dann KC said during the bail application.
Mr Dann argued there would likely be significant delays in the hearing as police were still waiting to hear back from the Qatar and Iceland governments.
Ghumman was unlikely to serve a sentence that reflected his potential time on remand, Mr Dann said.
Ghumman's father also put forward an $880,000 bail guarantee and had threatened to disinherit his son if he did not comply with his bail, Mr Dann said.
Justice Fox on Wednesday accepted the guarantee was in place but did not find that it was a compelling reason to release Ghumman.
She determined the allegations of stalking and intimidation were serious, and if convicted, Ghumman's sentence could be lengthy.
"The applicant has displayed a level of planning, obsession and determination which is concerning," Justice Fox said.
Ghumman also posed an unacceptable risk of endangering the safety of the victim and interfering with witnesses, the judge said.
She found no bail conditions could reduce that risk as she refused Ghumman bail and remanded him in custody.
He is due to return to Melbourne Magistrates Court for a committal mention hearing in October.
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