1999 NASCAR Winston Cup Series

The 1999 NASCAR Winston Cup season, the 51st season of professional in the United States, the 28th modern-era Cup series, and the last Cup season of the 1990s, the 20th century's final decade, 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.

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

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.

Race one: top ten results

Race two: top ten results

The 1999 Daytona 500 was held February 14 at Daytona International Speedway. Jeff Gordon won the pole. In winning the race as well, he became the first Daytona 500 pole sitter to win the race since Bill Elliott in 1987. This race is known for Gordon's daring three-wide pass on Rusty Wallace and Mike Skinner. Gordon passed Wallace after ducking to the apron, nearly plowing into the damaged car of Ricky Rudd. Skinner jumped to the outside and they raced three-wide for three laps until Dale Earnhardt gave Gordon the needed push. The race was also known for a determined Dale Earnhardt repeatedly trying to pass Jeff Gordon for the lead on the final lap, but Gordon beat Earnhardt to the finish. The race was also marked by a large crash on lap 135 in turn 3 that collected 13 cars and saw Dale Jarrett flip over twice.

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