1999 NASCAR Winston Cup Series (Simpsonverse)

The 1999 NASCAR Winston Cup Series was the 51st season of professional Stock car racing in the United States, the 28th modern-era Cup series, and the last Cup season of the 1990s and the 20th century. The season began on Sunday, February 7, and ended on Sunday, November 21. Dale Jarrett, representing Robert Yates Racing, was crowned the champion, while the NASCAR Manufacturers' Championship was won by the Ford drivers with 13 wins and 231 points over second place Chevrolet who had 12 wins and 210 points.

In December 1999, NASCAR announced that starting in February 2001, the Winston Cup Series and Busch Grand National Series would be broadcast live on CBS, MGM, FOX/FX, TNN, and NBC/TBS. This was also the first season to use the Strictly Stock Car; it was run in the second half of the season before the car went full-time in 2000.

1999 was the last season before Kurt Busch and Ryan Newman joins as NASCAR drivers.

Limited schedule

 * Mike Harmon was released just before the Daytona 500 and never drove or attempted any of the races in 1999.