1999 The 50th Pepsi Southern 500

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 at 270 laps – shortened from 367 laps due to rain – on the 1.366 mile (2.198 km) speedway, it was the 24th race of the 1999 NASCAR Winston Cup Series season. Jeff Burton of Roush Racing won the race.

Kenny Irwin, Jr. would earn his final pole position while qualifying for this event.

Race statistics

 * Time of race: 3:25:15
 * Average Speed: 107.816 mph
 * Pole Speed: 170.97
 * Cautions: 6 for 62 laps
 * Margin of Victory: under caution
 * Lead changes: 20
 * Percent of race run under caution: 23%
 * Average green flag run: 34.7 laps