Suggestions by @jameseller

Marty

as Best Picture 1956 in Oscars Do-over

David Lean

as Best Director 1956 in Oscars Do-over

Ernest Borgnine

as Best Actor 1956 in Oscars Do-over

Susan Hayward

as Best Actress 1956 in Oscars Do-over

Jack Lemmon

as Best Supporting Actor 1956 in Oscars Do-over

Peggy Lee

as Best Supporting Actress 1956 in Oscars Do-over

The Ten Commandments (1956)

as Best Picture 1957 in Oscars Do-over

William Wyler

as Best Director 1957 in Oscars Do-over

Kirk Douglas

as Best Actor 1957 in Oscars Do-over

Ingrid Bergman

as Best Actress 1957 in Oscars Do-over

Mickey Rooney

as Best Supporting Actor 1957 in Oscars Do-over

Eileen Heckart

as Best Supporting Actress 1957 in Oscars Do-over

12 Angry Men

as Best Picture 1958 in Oscars Do-over

Sidney Lumet

as Best Director 1958 in Oscars Do-over

Marlon Brando

as Best Actor 1958 in Oscars Do-over

Joanne Woodward

as Best Actress 1958 in Oscars Do-over

Arthur Kennedy

as Best Supporting Actor 1958 in Oscars Do-over

Miyoshi Umeki

as Best Supporting Actress 1958 in Oscars Do-over

Gigi

as Best Picture 1959 in Oscars Do-over

Mark Robson

as Best Director 1959 in Oscars Do-over