Businessman Eric Watson lost a long running dispute with Inland Revenue, with a High Court Judge ruling companies he owns are liable to pay $51.1 million in back taxes.
Justice Matthew Palmer ruled a transaction in 2002 - involving Cayman Island companies while Watson was relocating to the UK - was an avoidance arrangement, reports NZME.
Watson's Cullen Group is liable for back taxes, plus interest and penalties.
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During a trial last year, the court heard Inland Revenue calculated interest costs alone at $60.5 million.
Justice Palmer said penalties have yet to be quantified, NZME reported.
Last year, Watson was ordered by a UK court to pay close to $50 million NZD, after being taken to court by Sir Owen Glenn and Kea Investments over a joint European property venture called Spartan Capital.
The court found Watson had "planned and orchestrated" a scheme to trick Kea into entering agreements.
Kea invested £129 million into Spartan Capital.
Watson did not appeal the judgment, and was ordered to make an interim payment, as well as paying court costs.