The 1999 Winston 500 was the 30th race of the 1999 NASCAR Winston Cup Series season, held on Talladega Superspeedway over 188 laps.

Dale Earnhardt would collect his second to last Talladega win in this race.

PR: provisional Failed to qualify, withdrew, or driver changes:   Bobby Gerhart (#89), Robert Pressley (#77), Darrell Waltrip (#66), Hut Stricklin (#58)