The 1999 NAPA Autocare 500 was the 28th stock car race of the 1999 NASCAR Winston Cup Series season and the 51st iteration of the event. The race was held on Sunday, October 3, 1999, before an audience of 62,000 in Martinsville, Virginia at Martinsville Speedway, a 0.526 miles (0.847 km) permanent oval-shaped short track. The race took the scheduled 500 laps to complete. Within the final laps of the race, Hendrick Motorsports driver Jeff Gordon was able to hold off the field on the final restart with 19 to go to take his 48th career NASCAR Winston Cup Series victory and his sixth victory of the season. To fill out the top three, Richard Childress Racing driver Dale Earnhardt and Joe Bessey Racing driver Geoff Bodine would finish second and third, respectively.