Suggestions by @jameseller

Fredric March

as Best Actor 1938 in Oscars Do-over

Greta Garbo

as Best Actress 1938 in Oscars Do-over

Ralph Bellamy

as Best Supporting Actor 1938 in Oscars Do-over

Anne Shirley

as Best Supporting Actress 1938 in Oscars Do-over

Jezebel

as Best Picture 1939 in Oscars Do-over

Michael Curtiz

as Best Director 1939 in Oscars Do-over

Charles Boyer

as Best Actor 1939 in Oscars Do-over

Norma Shearer

as Best Actress 1939 in Oscars Do-over

John Garfield

as Best Supporting Actor 1939 in Oscars Do-over

Billie Burke

as Best Supporting Actress 1939 in Oscars Do-over

The Wizard of Oz

as Best Picture 1940 in Oscars Do-over

Victor Fleming

as Best Director 1940 in Oscars Do-over

Clark Gable

as Best Actor 1940 in Oscars Do-over

Judy Garland

as Best Actress 1940 in Oscars Do-over

Frank Morgan

as Best Supporting Actor 1940 in Oscars Do-over

Geraldine Fitzgerald

as Best Supporting Actress 1940 in Oscars Do-over

The Great Dictator

as Best Picture 1941 in Oscars Do-over

John Ford

as Best Director 1941 in Oscars Do-over

Henry Fonda

as Best Actor 1941 in Oscars Do-over

Ginger Rogers

as Best Actress 1941 in Oscars Do-over