The 1999 Goody's Headache Powder 500 was a NASCAR Winston Cup Series racing event that took place August 28, 1999, at Bristol Motor Speedway in 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.