Clive Wolman, from Islington, north London, said he was not subject to parking regulations because his motorbike balanced on its centre stand.
But three Court of Appeal Judges rejected his case, saying he had misinterpreted use of language.
He now stands to pay for up to 100 parking tickets plus legal costs.
Wolman would park his 500cc Suzuki on the pavement outside his home in Duncan Terrace, Islington, and at his office in Chancery Lane in the City.
He began his legal battle in May 2005 against the City of London Corporation and Islington Council, claiming damages for wrongful interference with his motorcycle, and harassment.
But Lord Justice Moore-Bick, giving the ruling of the Court of Appeal, said: "When parked in Chancery Lane in the manner I have described, his motorcycle can quite properly be said to be parked on the pavement, even if neither wheel is directly in contact with it."
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