Suggestions by @jameseller

Peggy Wood

as Best Supporting Actress 1966 in Oscars Do-over

Alfie

as Best Picture 1967 in Oscars Do-over

Richard Brooks

as Best Director 1967 in Oscars Do-over

Steve McQueen

as Best Actor 1967 in Oscars Do-over

Elizabeth Taylor

as Best Actress 1967 in Oscars Do-over

George Segal

as Best Supporting Actor 1967 in Oscars Do-over

Geraldine Page

as Best Supporting Actress 1967 in Oscars Do-over

Bonnie and Clyde

as Best Picture 1968 in Oscars Do-over

Mike Nichols

as Best Director 1968 in Oscars Do-over

Warren Beatty

as Best Actor 1968 in Oscars Do-over

Anne Bancroft

as Best Actress 1968 in Oscars Do-over

John Cassavetes

as Best Supporting Actor 1968 in Oscars Do-over

Carol Channing

as Best Supporting Actress 1968 in Oscars Do-over

Romeo and Juliet (1968 film)

as Best Picture 1969 in Oscars Do-over

Stanley Kubrick

as Best Director 1969 in Oscars Do-over

Alan Arkin

as Best Actor 1969 in Oscars Do-over

Patricia Neal

as Best Actress 1969 in Oscars Do-over

Jack Albertson

as Best Supporting Actor 1969 in Oscars Do-over

Ruth Gordon

as Best Supporting Actress 1969 in Oscars Do-over

Butch Cassidy And the Sundance Kid

as Best Picture 1970 in Oscars Do-over