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 2002 Subway 400 was the second stock car race of the 2002 NASCAR Winston Cup Series and the 37th iteration of the event. The race was held on Sunday, February 24, 2002, 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. At race's end, Matt Kenseth, driving for Roush Racing, would dominate the late stages of the race and win under caution when NASCAR determined oil and debris had made racing conditions unsafe with five to go. The win was Kenseth's second career NASCAR Winston Cup Series win and his first win of the season. To fill out the podium, Sterling Marlin of Chip Ganassi Racing and Bobby Labonte of Joe Gibbs Racing would finish second and third, respectively.
The 2000 Dura Lube/Kmart 400 was the second stock car race of the 2000 NASCAR Winston Cup Series and the 35th iteration of the event. The race was held on Sunday, February 27, 2000, in Rockingham, North Carolina at North Carolina Speedway, a 1.017 miles (1.637 km) permanent D-shaped oval racetrack. The race took the scheduled 393 laps to complete. At race's end, Bobby Labonte, driving for Joe Gibbs Racing, would hold off Dale Earnhardt and win after leading the final 113 laps. This was Labonte's 13th career NASCAR Winston Cup Series win and his first of the season. To fill out the podium, Dale Earnhardt of Richard Childress Racing and Ward Burton of Bill Davis Racing would finish second and third, respectively.
The 2000 Pepsi 400 was the 17th stock car race of the 2000 NASCAR Winston Cup Series and the 42nd iteration of the event. The race was held on Saturday, July 1, 2000, in Daytona Beach, Florida at Daytona International Speedway, a 2.5 miles (4.0 km) permanent triangular-shaped superspeedway. The race took the scheduled 160 laps to complete. At race's end, Jeff Burton, driving for Roush Racing, would fiercely defend the lead on the final restart with four to go to win a chaotic race. The win was Burton's 13th career NASCAR Winston Cup Series win and his second of the season. To fill out the podium, Dale Jarrett of Robert Yates Racing and Rusty Wallace of Penske-Kranefuss 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. This race marked the official debut of Jimmie Johnson in the cup series.
The 2001 Pop Secret Microwave Popcorn 400 was the 33rd stock car race of the 2001 NASCAR Winston Cup Series and the 37th iteration of the event. The race was held on Sunday, November 4, 2001, 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. At race's end, Joe Nemechek, driving for Andy Petree Racing, managed to dominate the late stages of the race to win his second career NASCAR Winston Cup Series victory and his only victory of the season. The other podium finishers were Kenny Wallace, driving for Dale Earnhardt, Inc., and Johnny Benson Jr., driving for MBV Motorsports, who placed second and third respectively.
The 2001 Old Dominion 500 was the 30th stock car race of the 2001 NASCAR Winston Cup Series and the 53rd iteration of the event. The race was held on Monday, October 15, 2001, 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 closing laps of the race, Ricky Craven, driving for PPI Motorsports, would manage to defend Robert Yates Racing driver Dale Jarrett in a close finish to win his first career NASCAR Winston Cup Series victory and his only victory of the season. To fill out the podium, Jarrett and Bill Davis Racing driver Ward Burton 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 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 Goody's Body Pain 500 was the eighth stock car race of the 1999 NASCAR Winston Cup Series season and the 50th iteration of the event. The race was held on Sunday, April 18, 1999, before an audience of 60,000 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. With three laps to go in the race, Petty Enterprises driver John Andretti would make a late-race move for the lead on Roush Racing driver Jeff Burton to take his second and final career NASCAR Winston Cup Series victory and his only win of the season. To fill out the podium, Jeff Burton and Hendrick Motorsports driver Jeff Gordon 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 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 originally scheduled to be held on Sunday, October 10, 1999, but was delayed to Monday, October 11 due to inclement weather. The race was held in front of an audience of 125,000 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. In the closing laps of the race, Hendrick Motorsports driver Jeff Gordon would manage to close in and pass for the lead with eight to go to take his 49th career NASCAR Winston Cup Series victory and his seventh and final victory of the season. To fill out the podium, Joe Gibbs Racing driver Bobby Labonte and Richard Childress Racing driver Mike Skinner would finish second and third, respectively.
The 2000 Pop Secret Microwave Popcorn 400 was the 31st stock car race of the 2000 NASCAR Winston Cup Series and the 36th iteration of the event. The race was held on Sunday, October 22, 2000, 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 43 laps of the race, Robert Yates Racing driver Dale Jarrett would manage to make a pass for the lead and defend the field to take his 24th career NASCAR Winston Cup Series victory and his second and final victory of the season. To fill out the top 3, Hendrick Motorsports driver Jeff Gordon and Robert Yates Racing driver Ricky Rudd would finish second and third, respectively.
The 1999 NAPA Autocare 500 was the 28th stock car race of the 1999 NASCAR Winston Cup Series season and the 51st iteration of the event. The race was held on Sunday, October 3, 1999, before an audience of 62,000 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. Within the final laps of the race, Hendrick Motorsports driver Jeff Gordon was able to hold off the field on the final restart with 19 to go to take his 48th career NASCAR Winston Cup Series victory, his sixth victory of the season and it marked Gordon's first race & win without Ray Evernham as his crew chief. To fill out the top three, Richard Childress Racing driver Dale Earnhardt and Joe Bessey Racing driver Geoff Bodine would finish second and third, respectively.
The 2002 Pop Secret Microwave Popcorn 400 was the 34th stock car race of the 2002 NASCAR Winston Cup Series and the 38th iteration of the event. The race was held on Sunday, November 3, 2002, 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, MBV Motorsports driver Johnny Benson Jr. would manage to defend for the lead within the last 26 laps of the race to take his first and only NASCAR Winston Cup Series victory and his only victory of the season. To fill out the top three, Mark Martin and Kurt Busch, both drivers for Roush Racing, would finish second and third, respectively.
