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. Tony Stewart of Joe Gibbs Racing won the race.
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