The 1999 Pennzoil 400 Presented by Kmart was an inaugural NASCAR Winston Cup Series race held on November 14, 1999 at Homestead Miami Speedway in Homestead, Florida. Contested over 267 laps on the 1.5 mile (2.4 km) speedway, it was the 33rd race of the 1999 NASCAR Winston Cup Series season and the first at Homestead-Miami Speedway. Tony Stewart of Joe Gibbs Racing won the race, his teammate Bobby Labonte finished second and Roush Racing driver Jeff Burton was third. This was the last race without Dale Earnhardt Jr. until the 2012 Bank of America 500.