The 1999 The 50th Pepsi Southern 500, the 50th running of the event, was a NASCAR Winston Cup Series race held on September 5, 1999, at Darlington Raceway in Darlington County, South Carolina. Contested over 270 laps â shortened from 367 laps due to rain â on the speedway, it was the 24th race of the 1999 NASCAR Winston Cup Series season. Jeff Burton of Roush Racing won the race, and the No Bull 5 Million Dollar Bonus as well.
Kenny Irwin Jr. would earn his final pole position while qualifying for this event.