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Runners up: Five persons have each won three Oscars for acting: (1) Walter Brennan won three Oscars for Bes â¦ t Supporting Actor; (2) Ingrid Bergman won two Best Actress Oscars and one for Best Supporting Actress; (3) Jack Nicholson won two Oscars for Best Actor and one Oscar for Best Supporting Actor; (4) Meryl Streep won two Best Actress Oscars and one for Best Supporting Actress; (5) Daniel Day-Lewis became the first person ever to win three Oscars for Best Actor.