Leeds United chairman Ken Bates must pay £10,000 to ex-director Melvyn Levi, for allegedly likening him to a criminal.
Mr Levi claims the businessman, the club and a local radio station pursued a campaign against him and his wife, Carole.
Judge Mark Gosnell at Leeds County Court ordered Mr Bates to pay Mr Levi the sum because of the stress caused by Mr Bates’ harassment.
Mr Levi and his wife also claimed that Mr Bates had made hints in his match day programme notes about the state of their marriage. A separate claim by Mrs Levi was dismissed.
Mr Levi was part of a consortium which ran the club before Mr Bates took over in 2005. In July 2009 Mr Levi was awarded £50,000 in libel damages after Mr Bates described him as a "shyster" in his column in the programme.