How many Oscars has Clint Eastwood won? ChaCha Answer: Clint Eastwood has won 4 Oscars. 2 for Million Dollar Baby and 2 for Unforgiven. 0 7 years ago Clint Eastwood Awards: Won 4 Oscars and 5 Golden Globes, Born: 31 May 1930 Where: San Francisco, California, Height: 6' 4