Which movie has won the most Oscars and how many did it win? July 30, 2020 by Pamela Landy Ben-Hur with 11 Oscars was the biggest winner in 1989. Related Answers Who was the first actor or actress to win three Academy Awards? When did Spiro Agnew resign from the vice-presidency? What was the first movie to win all five top Oscars? How many Oscars did Humphrey Bogart win? How many Oscars has screenwriter Robert Bolt won? How many directing Oscars did Alfred Hitchcock win?