Jagpal Singh, who claimed squatters' rights on the flat, applied to the District Court for possession of the residence at Nation Street, saying he had lived there since he was born in 1977.
Singh won Hong Kong dollars 44.3 million when he took a one-third share of a local lottery company's biggest ever rollover jackpot in 2011.
But his luck ran out when he tried to claim squatters' rights on the flat, the South China Morning Post reported today.
The counsel for the flat's owner, Yu King-chau, told the court Yu was seeking vacant possession of the home and payment of the rent Singh had failed to cough up over the years.
A writ filed by Yu in December 2011, seven months after Singh won the lottery, said the man's parents had rented the flat from Yu's mother Kwong Mei-heung, who died in 1981.
They continued to pay rent into an account in Kwong's name until 1995, when the rent was about Hong Kong dollars 1,500 a month.
Believing Yu's rights to the flat had expired, Singh, whose mother died in 2008, asked the court to declare him its owner.
But lawyers for Yu, who was granted probate on the flat in July 2011, told the court he would file a counter claim against the Singh seeking rent and possession of the flat.
Deputy Judge Lawrence Yip Sue-pui adjourned the case till May 14.
After winning the lottery, Singh pledged to continue working as a delivery driver. Chinese-language newspapers reported last year that Singh had spent part of his new fortune on three flats at Caribbean Coast in Tung Chung, from which he was earning over Hong Kong dollars 40,000 a month in rent.
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