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The 27th International 500-Mile Sweepstakes Race was held at the Indianapolis Motor Speedway on May 30, 1939. The race was won by the number two car of Wilbur Shaw, who started in the third position, driving a Maserati 8CTF. The race was notable for a three car accident on lap 109, when Floyd Roberts, the reigning champion, was killed when his car went through the wooden outer wall at over 100 miles (160 km) an hour at the backstretch. In Louis Meyer's final Indy 500, he too would crash at the backstretch at over 100 miles (160 km) an hour, but he walked away unharmed.

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