The 1999 Goody's Headache Powder 500 was a NASCAR Winston Cup Series racing event that took place August 28, 1999, at Bristol International Speedway in the American community of Bristol, Tennessee.
The race was the 23rd of the 1999 NASCAR Winston Cup Series season. The pole position was held by Joe Gibbs Racing's Tony Stewart, who also led the most laps with 225. The race winner was Dale Earnhardt of Richard Childress Racing, who started 26th, the lowest starting position for a winner at Bristol.
The early part of the race was primarily dominated by Tony Stewart, but Terry Labonte and Dale Earnhardt dominated the later half, with the two trading the lead seven times starting on lap 300 when Terry Labonte passed Jeff Gordon. Earnhardt took the lead for the first time on lap 380. On lap 410, the caution flew after Dave Marcis' car stopped against the turn-2 wall. Upon the caution flag waving, Marcis proceeded to drive away, and as Marcis was frequently aided by Richard Childress Racing, suspicions arose over whether or not Marcis intentionally caused a caution. NASCAR then penalized Marcis, and made him stay in pit road for a lap; NASCAR stated that Marcis claimed he couldn't reach pit road, and had to stop. However, NASCAR said Marcis had a chance to reach pit road on the two laps he was driving slowly before stopping. On the restart, Terry Labonte led the race, and on lap 435, Earnhardt passed Labonte for the lead. However, Labonte then passed Earnhardt with 57 laps left, but on lap 490, Labonte slowed down, and was spun by Darrell Waltrip, giving the lead back to Earnhardt.
Labonte then pitted for new tires, and eventually, with five laps remaining, Labonte contested Earnhardt for the lead, setting up the finish. Terry Labonte was leading on the last lap, but he was spun by Earnhardt in turn 2, and Earnhardt secured his ninth victory at Bristol. Jimmy Spencer finished second, followed by Ricky Rudd, Jeff Gordon and Stewart. Labonte finished in 8th, and one lap down. Earnhardt's victory was subsequently met by boos from the crowd, probably one of the few if not only time this happened. NASCAR officials reviewed the pass, but decided to let Earnhardt keep the victory. Earnhardt later stated, "I didn’t mean to wreck him, I just wanted to rattle his cage a bit." A similar incident between Earnhardt and Labonte had occurred four years prior, at the Goody's 500; Earnhardt turned Labonte sideways, and Labonte was pushed by Earnhardt past the finish line sideways, giving Labonte the win.