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Malaysian-born, Mr Chai (23) moved to New Zealand in 2011, gained a bachelor of visual arts at Auckland University of Technology (AUT) last year, and has already made a habit of winning art awards.
"I’m just very humbled," Mr Chai said after the National Cleveland Awards were announced at the society’s home at Dunedin Railway Station yesterday.
Mr Chai’s haunting realist art work Howick won a new youth award, and an excellence award in painting, as well as the show’s overall $4000 supreme award, earning him $5500 overall.
Society president Doug Hart said it was "a special moment" and"unprecedented" for three award categories to be won at the same society show since they began in 1876, and he urged members of the public to see the free show, comprising 185 works, which runs until June 12.
The oil on linen supreme award-winning work has also sold for $1500.