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. 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, a series of Winston Cup and Grand Nationa ...
The 1999 Brickyard 400, the 6th running of the event, was a NASCAR Winston Cup Series race held on August 7, 1999 at Indianapolis Motor Speedway in Speedway, Indiana. Contested at 160 laps on the 2.5 mile speedway, it was the 20th race of the 1999 NASCAR Winston Cup Series season. Dale Jarrett of Robert Yates Racing won the race.
The 1999 Daytona 500, the 41st running of the event, was held February 14, 1999, at Daytona International Speedway. Jeff Gordon won the pole and won the race, making him the first Daytona 500 pole sitter to win the race since Bill Elliott in 1987.
The 1999 Frontier the Glen was a NASCAR Winston Cup Series race held at Watkins Glen International, Watkins Glen, New York on April 15, 1999. It was the 21st points-paying event of the 1999 NASCAR Winston Cup Series season. Rusty Wallace won the pole, and Jeff Gordon won the race for the third consecutive year. A total of 49 cars attempted the race.
The 1999 Goodys Headache Powder 500 was a NASCAR Winston Cup Series racing event that took place August 28, 1999, at Bristol International Speedway in Bristol, Tennessee. The race was the 23rd season of the Cup series, 1999 NASCAR Winston. The pole position was held by Joe Gibbs racing Tony Stewart, who led the most laps with 225. The winner of the race was Dale Earnhardt Richard Childress racing, which launched on the 26th, the lowest starting position for a winner in Bristol.
The 1999 NAPA 500 was a NASCAR Winston Cup Series racing event held on November 21, 1999, at Atlanta Motor Speedway in the American community of Hampton, Georgia.
The 1999 Save Mart/Kragen 350 was a NASCAR Winston Cup Series race held at Sears Point Raceway, Sonoma, California on June 27, 1999. It was the 16th points-paying event of the 1999 NASCAR Winston Cup Series season. Jeff Gordon won the pole race for the second consecutive year. A total of 51 cars attempted the race.
The 1999 The 50th Pepsi Southern 500, the 50th running of the event, was a NASCAR Winston Cup Series race held on September 5, 1999 at Darlington Raceway in Darlington County, South Carolina. Contested at 270 laps – shortened from 367 laps due to rain – on the 1.366 mile speedway, it was the 24th race of the 1999 NASCAR Winston Cup Series season. Jeff Burton of Roush Racing won the race. Kenny Irwin Jr. would earn his final pole position during qualifying for the event.
The 1999 TranSouth Financial 400 was a NASCAR Winston Cup Series race held at Darlington Raceway, Darlington, South Carolina on March 21, 1999. Jeff Burton won the race.