Mr Gaines-Cooper, who made his fortune from renting out jukeboxes in the 1960s, is being pursued for taxes relating to the period 1992-2004.
He argued that since he left Britain for the Seychelles in 1976, he has obeyed the rule that gives non-resident status and tax benefits to anyone who spends less than 90 days a year in the country.
However, High Court and Appeal Court judges ruled he had not made a "clean break", citing a family house in Henley-on-Thames, a UK-based collection of classic Rolls-Royces and trips to Ascot.
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