Suggestions by @jameseller

Sam Wood

as Best Director 1943 in Oscars Do-over

James Cagney

as Best Actor 1943 in Oscars Do-over

Katharine Hepburn

as Best Actress 1943 in Oscars Do-over

Walter Huston

as Best Supporting Actor 1943 in Oscars Do-over

Susan Peters

as Best Supporting Actress 1943 in Oscars Do-over

Casablanca (film)

as Best Picture 1944 in Oscars Do-over

Henry King

as Best Director 1944 in Oscars Do-over

Mickey Rooney

as Best Actor 1944 in Oscars Do-over

Joan Fontaine

as Best Actress 1944 in Oscars Do-over

Charles Coburn

as Best Supporting Actor 1944 in Oscars Do-over

Paulette Goddard

as Best Supporting Actress 1944 in Oscars Do-over

Otto Preminger

as Best Director 1945 in Oscars Do-over

Cary Grant

as Best Actor 1945 in Oscars Do-over

Bette Davis

as Best Actress 1945 in Oscars Do-over

Barry Fitzgerald

as Best Supporting Actor 1945 in Oscars Do-over

Jennifer Jones

as Best Supporting Actress 1945 in Oscars Do-over

Spellbound

as Best Picture 1946 in Oscars Do-over

Clarence Brown

as Best Director 1946 in Oscars Do-over

Gene Kelly

as Best Actor 1946 in Oscars Do-over

Greer Garson

as Best Actress 1946 in Oscars Do-over