The 1999 The 50th Pepsi Southern 500 was a Winston Cup (now Nextel Cup) event held at Darlington Raceway on August 22, 1999. It might have been a repeat of the spring event. Jeff Burton was pulling away to a strong victory over brother Ward when rain clinched Burton's victory. Dale Jarrett struggled to 14th and now watched his points lead shrink to 168 markers on Mark Martin (4th). Stats