The Telegraph published two articles on 23 April under the headlines "World's worst tennis pro wins at last" and "A British sensation - the world's worst".
Dee reportedly argued that the articles in the paper suggested "that he unreasonably and unrealistically persists in a career as a professional tennis player, which is an expensive waste of money and doomed to failure".
Dee's barrister Andrew Caldecott QC said that the Telegraph articles ridiculed and embarrassed the player. He added that they could deter people from hiring Dee as a professional coach.
The paper has refused to back down over the two articles. It insisted in the court that Dee holds the dubious honour of having had the world's worst losing run in professional tennis.
Dee has reportedly received over 30 apologies and huge amounts in damages from various media organisations that made similarly disparaging statements about his career, including the BBC, Daily Mail, Guardian and Sun.