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.

[2] David Green would earn his only pole position during qualifying.

[3] On the 228th lap, Stewart overtook Labonte for the first position, and later went on to win the event,[2] his third career triumph in the Cup Series.

[7] Drivers' Championship leader Dale Jarrett had a lead of 231 points entering the race,[8] and his fifth place finish was enough to clinch the championship, and claim his first (and only) NASCAR Cup Series title, leading by 211 points at the checkered flag.

[2] There was a single caution and a total of nineteen lead changes amongst ten different drivers during the course of the race.