The 1999 TranSouth Financial 400 was the fifth stock car race of the 1999 NASCAR Winston Cup Series season and the 43rd iteration of the event. The race was held on Sunday, March 21, 1999, before an audience of 71,000 in Darlington, South Carolina, at Darlington Raceway, a 1.366 miles (2.198 km) permanent egg-shaped oval racetrack. The race was shortened from its scheduled 293 laps to 164 due to rain. In the final laps of the race, a wreck involving five cars, including the leader at the time, Roush Racing driver Jeff Burton would occur in the midst of rain on lap 163. Despite major damage to his car, Burton would manage to keep up with pace car speed and when the race was stopped a lap later due to increasing rain, NASCAR decided to let the race end due to a lack of sunlight. The victory was Burton's seventh career NASCAR Winston Cup Series victory and his second victory of the season. To fill out the top three, Penske-Kranefuss Racing driver Jeremy Mayfield and Hendrick Motorsports driver Jeff Gordon would finish second and third, respectively.
The 2000 DirecTV 500 was the seventh stock car race of the 2000 NASCAR Winston Cup Series and the fourth iteration of the event. The race was held on Sunday, April 2, 2000, before an audience of 223,000 in Fort Worth, Texas at Texas Motor Speedway, a 1.5 miles permanent tri-oval shaped racetrack. The race took the scheduled 334 laps to complete. At race's end, Dale Earnhardt, Inc.'s Dale Earnhardt Jr. managed to dominate the final stages of the race, leading the final 53 laps of the race to take his first career NASCAR Winston Cup Series victory and his first victory of the season. To fill out the top three, Roush Racing's Jeff Burton and Joe Gibbs Racing's Bobby Labonte finished second and third, respectively.
The 2000 UAW-GM Quality 500 was the 29th stock car race of the 2000 NASCAR Winston Cup Series and the 41st iteration of the event. The race was held on Sunday, October 8, 2000, before an audience of 140,000 in Concord, North Carolina, at Charlotte Motor Speedway, a 1.5 miles (2.4 km) permanent quad-oval. The race took the scheduled 334 laps to complete. In the final laps of the race, Joe Gibbs Racing's Bobby Labonte managed to make a late-race pass for the lead, assisted by a late four-tire pit stop. The victory was Labonte's 15th career NASCAR Winston Cup Series victory and his fourth and final victory of the season. To fill out the top three, Penske-Kranefuss Racing's Jeremy Mayfield and Robert Yates Racing's Ricky Rudd finished second and third, respectively.
The 2000 Pepsi 400 presented by Meijer was the 22nd stock car race of the 2000 NASCAR Winston Cup Series and the 31st iteration of the event. The race was held on Sunday, August 20, 2000, in Brooklyn, Michigan, at Michigan International Speedway, a two-mile moderate-banked D-shaped speedway. The race took the scheduled 200 laps to complete. At race's end, Penske-Kranefuss Racing driver Rusty Wallace, with the help of his crew chief, would pull away on the final restart with 18 to go to win his 52nd career NASCAR Winston Cup Series win and his third of the season. To fill out the podium, Ricky Rudd of Robert Yates Racing and Bobby Labonte of Joe Gibbs Racing would finish second and third, respectively.
The 2000 NAPA Autocare 500 was the 28th stock car race of the 2000 NASCAR Winston Cup Series and the 52nd iteration of the event. The race was held on Sunday, October 1, 2000, in Ridgeway, Virginia, at Martinsville Speedway, a 0.526 miles (0.847 km) permanent oval-shaped short track. The race took the scheduled 500 laps to complete. At race's end, Tony Stewart, driving for Joe Gibbs Racing, would control the final restart with 11 laps to go to win his eighth career NASCAR Winston Cup Series win and his fifth of the season. To fill out the podium, Dale Earnhardt of Richard Childress Racing and Jeff Burton of Roush Racing would finish second and third, respectively.
The 2001 UAW-GM Quality 500 was the 29th stock car race of the 2001 NASCAR Winston Cup Series and the 42nd iteration of the event. The race was held on Sunday, October 7, 2001, in Concord, North Carolina, at Lowe's Motor Speedway, a 1.5 miles (2.4 km) permanent quad-oval. The race took the scheduled 334 laps to complete. At race's end, Sterling Marlin, driving for Chip Ganassi Racing with Felix Sabates, would dominate the late stages of the race to win his eighth career NASCAR Winston Cup Series victory and his second and final victory of the season. To fill out the podium, Tony Stewart, driving for Joe Gibbs Racing, and Ward Burton, driving for Bill Davis Racing, would finish second and third, respectively.
The 2001 NAPA 500 was the 35th stock car race of the 2001 NASCAR Winston Cup Series and the 42nd iteration of the event. The race was held on Sunday, November 18, 2001, in Hampton, Georgia at Atlanta Motor Speedway, a 1.54 miles (2.48 km) permanent asphalt quad-oval intermediate speedway. The race took the scheduled 325 laps to complete. On the final lap of the race, Jerry Nadeau, driving for Hendrick Motorsports, would run out of fuel heading into turn 3, leading to Joe Gibbs Racing driver Bobby Labonte stealing the victory away from Nadeau. The win was Labonte's 18th career NASCAR Winston Cup Series victory and his second and final victory of the season. To fill out the podium, Sterling Marlin, driving for Chip Ganassi Racing with Felix Sabates, and Kevin Harvick, driving for Richard Childress Racing, would finish second and third, respectively.
The 2003 UAW-GM Quality 500 was the 31st stock car race of the 2003 NASCAR Winston Cup Series season and the 44th iteration of the event. The race was held on Saturday, October 11, 2003, before a crowd of 160,000 in Concord, North Carolina, at Lowe's Motor Speedway, a 1.5 miles (2.4 km) permanent quad-oval. The race took the scheduled 334 laps to complete. At race's end, Tony Stewart, driving for Joe Gibbs Racing, would make a late race pass on Penske Racing South driver Ryan Newman with eight to go to win his 17th career NASCAR Winston Cup Series victory and his second and final win of the season. To fill out the podium, Ryan Newman and Hendrick Motorsports driver Jimmie Johnson would finish second and third, respectively.
The 1999 Dura Lube/Big K 400 was the second stock car race of the 1999 NASCAR Winston Cup Series season and the 34th iteration of the event. The race was held on Sunday, February 21, 1999, in Rockingham, North Carolina, at North Carolina Speedway, a 1.017 miles (1.637 km) permanent high-banked racetrack. The race took the scheduled 393 laps to complete. In the closing laps of the race, Roush Racing driver Mark Martin would manage to pull away with nine to go to win his 30th career NASCAR Winston Cup Series victory and his first victory of the season. To fill out the podium, Robert Yates Racing driver Dale Jarrett and Joe Gibbs Racing driver Bobby Labonte would finish second and third, respectively.
The 1999 Las Vegas 400 was the third stock car race of the 1999 NASCAR Winston Cup Series season, the second of five No Bull 5 races of the 1999 season, and the second iteration of the event. The race was held on Sunday, March 7, 1999, in North Las Vegas, Nevada at Las Vegas Motor Speedway, a 1.5 miles (2.4 km) permanent D-shaped oval racetrack. The race took the scheduled 267 laps to complete. In the closing laps of the race, Roush Racing driver Jeff Burton would manage to be victorious in a battle with Bill Davis Racing driver and brother Ward Burton to win his sixth career NASCAR Winston Cup Series victory and his first of the season. To fill out the podium, Ward Burton and Hendrick Motorsports driver Jeff Gordon would finish second and third, respectively.
The 1999 Cracker Barrel 500 was the fourth stock car race of the 1999 NASCAR Winston Cup Series season and the 40th iteration of the event. The race was held on Sunday, March 14, 1999, in Hampton, Georgia at Atlanta Motor Speedway, a 1.54 miles (2.48 km) permanent asphalt quad-oval intermediate speedway. The race took the scheduled 325 laps to complete. In the closing laps of the race, Hendrick Motorsports driver Jeff Gordon would manage to pull a sizable lead over the rest of the field to win his 44th career NASCAR Winston Cup Series victory and his second of the season. To fill out the podium, Joe Gibbs Racing driver Bobby Labonte and Roush Racing driver Mark Martin would finish second and third, respectively.
The 1999 Primestar 500 was the sixth stock car race of the 1999 NASCAR Winston Cup Series season and the third iteration of the event. The race was held on Sunday, March 28, 1999, in Fort Worth, Texas at Texas Motor Speedway, a 1.5 miles permanent tri-oval shaped racetrack. The race took the scheduled 334 laps to complete. Nearing the end of the race, Hendrick Motorsports driver Terry Labonte would make a late-race move to pass Robert Yates Racing driver Dale Jarrett for the lead. With three to go, the caution would come out for Jimmy Spencer, handing the win to Labonte. The win was Labonte's 21st career NASCAR Winston Cup Series victory and his only victory of the season. To fill out the podium, Jarrett and Joe Gibbs Racing driver Bobby Labonte would finish second and third, respectively.
The 1999 Food City 500 was the seventh stock car race of the 1999 NASCAR Winston Cup Series season and the 39th iteration of the event. The race was held on Sunday, April 11, 1999, in Bristol, Tennessee at Bristol Motor Speedway, a 0.533 miles (0.858 km) permanent oval-shaped racetrack. The race took the scheduled 500 laps to complete. At race's end, Penske-Kranefuss Racing driver Rusty Wallace would dominate most of the race to take home his 49th career NASCAR Winston Cup Series victory and his only win of the season. To fill out the podium, Roush Racing driver Mark Martin and Robert Yates Racing driver Dale Jarrett would finish second and third, respectively.
The 1999 MBNA Platinum 400 was the 13th stock car race of the 1999 NASCAR Winston Cup Series season and the 31st iteration of the event. The race was held on Sunday, June 6, 1999, in Dover, Delaware at Dover International Speedway, a 1-mile (1.6 km) permanent oval-shaped racetrack. The race took the scheduled 400 laps to complete. Depending on fuel mileage, Joe Gibbs Racing driver Bobby Labonte would manage to save enough fuel to almost lap the field to win his eighth career NASCAR Winston Cup Series victory and his first of the season. To fill out the podium, Hendrick Motorsports driver Jeff Gordon and Roush Racing driver Mark Martin would finish second and third, respectively.
The 1999 Kmart 400 presented by Castrol Super Clean was the 14th stock car race of the 1999 NASCAR Winston Cup Series season and the 31st iteration of the event. The race was held on Sunday, June 13, 1999, in front of an audience of 125,000 in Brooklyn, Michigan, at Michigan International Speedway, a two-mile (3.2 km) moderate-banked D-shaped speedway. The race took the scheduled 200 laps to complete. In a caution-free race, Robert Yates Racing driver Dale Jarrett would dominate for most of the race to take his 20th career NASCAR Winston Cup Series victory and his second of the season. To fill out the podium, Hendrick Motorsports driver Jeff Gordon and Roush Racing driver Jeff Burton would finish second and third, respectively.
The 1999 Pennsylvania 500 was the 19th stock car race of the 1999 NASCAR Winston Cup Series season and the 27th iteration of the event. The race was held on Sunday, July 25, 1999, in front of an audience of 95,000 in Long Pond, Pennsylvania, at Pocono Raceway, a 2.5 miles (4.0 km) triangular permanent course. The race took the scheduled 200 laps to complete. In the final stages of the race, Joe Gibbs Racing driver Bobby Labonte would manage to dominate and pull out to a healthy lead to win his tenth career NASCAR Winston Cup Series victory and his third victory of the season. To fill out the podium, Robert Yates Racing driver Dale Jarrett and Roush Racing driver Mark Martin would finish second and third, respectively.
The 1999 MBNA Gold 400 was the 27th stock car race of the 1999 NASCAR Winston Cup Series season and the 31st iteration of the event. The race was held on Sunday, September 26, 1999, in Dover, Delaware at Dover International Speedway, a 1-mile (1.6 km) permanent oval-shaped racetrack. The race took the scheduled 400 laps to complete. Roush Racing driver Mark Martin would manage to dominate the late stages of the race from lap 349 to take his 31st career NASCAR Winston Cup Series victory and his second and final victory of the season. To fill out the podium, Joe Gibbs Racing driver Tony Stewart and Robert Yates Racing driver Dale Jarrett would finish second and third, respectively.
The 1999 Pop Secret Microwave Popcorn 400 was the 31st stock car race of the 2001 NASCAR Winston Cup Series and the 25th iteration of the event. The race was held on Sunday, October 24, 1999, before an audience of 50,000 in Rockingham, North Carolina, at North Carolina Speedway, a 1.017 miles (1.637 km) permanent high-banked racetrack. The race took the scheduled 393 laps to complete. In the final laps of the race, Roush Racing driver Jeff Burton would manage to pull away from the field with 68 to go to win his 11th career NASCAR Winston Cup Series victory and his sixth and final victory of the season. To fill out the podium, Bill Davis Racing driver Ward Burton and Joe Gibbs Racing driver Bobby Labonte would finish second and third, respectively.
The 2003 Virginia 500 was the ninth stock car race of the 2003 NASCAR Winston Cup Series season and the 54th iteration of the event. The race was held on Sunday, April 13, 2003, before an audience of 86,000 in Martinsville, Virginia at Martinsville Speedway, a 0.526 miles (0.847 km) permanent oval-shaped short track. The race took the scheduled 500 laps to complete. In the final laps of the race, Hendrick Motorsports driver Jeff Gordon would manage to pass Joe Gibbs Racing driver Bobby Labonte to capture his 62nd career NASCAR Winston Cup Series victory and his first victory of the season. To fill out the top three, Labonte and Dale Earnhardt, Inc. driver Dale Earnhardt Jr. would finish second and third, respectively.
The 1999 edition of The Winston was the second exhibition stock car race of the 1999 NASCAR Winston Cup Series and the 15th iteration of the event. The race was held on Saturday, May 22, 1999, before an audience of 120,000 in Concord, North Carolina at Lowe's Motor Speedway, a 1.5 miles permanent quad-oval. The race took the scheduled 90 laps to complete. At race's end, Hendrick Motorsports driver Terry Labonte would make a late-race gamble on a pitstop, taking four tires. With five laps to go, he would charge to the front and defend the field, securing his second straight and consecutive The Winston victory. To fill out the top three, Joe Gibbs Racing driver Tony Stewart and Hendrick Motorsports driver Jeff Gordon would finish second and third, respectively.
