1999 NASCAR Winston Cup Series

The 1999 NASCAR Winston Cup season began on Sunday, February 7, and ended on Sunday, November 21. Dale Jarrett, representing Robert Yates Racing, was crowned the champion. 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.

Teams and drivers

Complete schedule

Limited schedule

Bud Shootout

The exhibition Bud Shootout race, for drivers who had won a pole position in the previous season or had won the event before, was held on February 7 at Daytona International Speedway. Rusty Wallace drew the pole.

Top ten results

Gatorade Twin 125's

The Gatorade Twin 125's, a pair of qualifying races for the Daytona 500, were held February 11 at Daytona International Speedway. Jeff Gordon and Tony Stewart won the pole positions for the races, respectively.

Sprint Cup Series

The NASCAR Sprint Cup Series (often shortened to Sprint Cup or the Cup Series) is the top racing series of the National Association for Stock Car Auto Racing (NASCAR). The series is named for its current sponsor, the Sprint Corporation, and has been known by other names in the past. It was originally known as the Strictly Stock Series (1949) and shortly became the Grand National Series (1950–1970). While leasing its naming rights to R. J. Reynolds Tobacco Company, it was known as the Winston Cup Series (1971–2003). A similar deal was made with Nextel in 2003, becoming the Nextel Cup Series (2004–2007) and it became the Sprint Cup after Sprint acquired Nextel in 2005. The name "Sprint" refers specifically to the subsidiary of Japanese telecommunications company SoftBank which is the entitlement sponsor; sprint car racing is a separate racing discipline.

The drivers' champion is determined by a point system where points are given according to finishing placement and laps led. The season is divided into two segments. After the first 26 races, 16 drivers, selected primarily on the basis of wins during the first 26 races, are seeded based on their total number of wins and compete in the last 10 races with the difference in points greatly minimized. This is called the Chase for the Championship.