Suggestions by @jameseller

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

Spencer Tracy

as Best Actor 1959 in Oscars Do-over

Shirley MacLaine

as Best Actress 1959 in Oscars Do-over

Burl Ives

as Best Supporting Actor 1959 in Oscars Do-over

Maureen Stapleton

as Best Supporting Actress 1959 in Oscars Do-over

Ben-Hur (1959)

as Best Picture 1960 in Oscars Do-over

Billy Wilder

as Best Director 1960 in Oscars Do-over

Charlton Heston

as Best Actor 1960 in Oscars Do-over

Doris Day

as Best Actress 1960 in Oscars Do-over

Arthur O'Connell

as Best Supporting Actor 1960 in Oscars Do-over

Thelma Ritter

as Best Supporting Actress 1960 in Oscars Do-over

The Magnificent Seven (1960)

as Best Picture 1961 in Oscars Do-over

John Sturges

as Best Director 1961 in Oscars Do-over

Yul Brynner

as Best Actor 1961 in Oscars Do-over

Deborah Kerr

as Best Actress 1961 in Oscars Do-over