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 2002 Old Dominion 500 was the 32nd stock car race of the 2002 NASCAR Winston Cup Series and the 54th iteration of the event. The race was held on Sunday, October 20, 2002, before a crowd of 87,000 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. At race's end, Kurt Busch, driving for Roush Racing, would come back from a dismal starting spot and spin to control the late stages of the race and win. The win was Busch's second career NASCAR Winston Cup Series victory and his second victory of the season. To fill out the podium, Johnny Benson Jr., driving for MBV Motorsports, and Ricky Rudd, driving for Robert Yates Racing, would finish second and third, respectively.
The 2003 Subway 500 was the 32nd stock car race of the 2003 NASCAR Winston Cup Series season and the 55th iteration of the event. The race was held on Sunday, October 19, 2003, before a crowd of 88,000 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. At race's end, Jeff Gordon, driving for Hendrick Motorsports, would dominate most of the race weekend to win his 63rd career NASCAR Winston Cup Series victory and his second of the season. To fill out the podium, Jimmie Johnson, driving for Hendrick Motorsports, and Tony Stewart, driving for Joe Gibbs Racing, would finish 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 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 DieHard 500 was the ninth stock car race of the 1999 NASCAR Winston Cup Series season and the 30th iteration of the event. The race was held on Sunday, April 25, 1999, before an audience of 100,000 in Lincoln, Alabama at Talladega Superspeedway, a 2.66 miles permanent triangle-shaped superspeedway. The race took the scheduled 188 laps to complete. In the final laps of the race, Richard Childress Racing driver Dale Earnhardt would manage to hold off the field on the final restart with 15 to go to win his 72nd career NASCAR Winston Cup Series victory and his first 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 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 Checker Auto Parts/Dura Lube 500k was the 32nd stock car race of the 1999 NASCAR Winston Cup Series and the 12th iteration of the event. The race was held on Sunday, November 7, 1999, before an audience of 78,000 in Avondale, Arizona at Phoenix International Raceway, a 1-mile (1.6 km) permanent low-banked tri-oval race track. The race took the scheduled 312 laps to complete. Joe Gibbs Racing driver Tony Stewart would manage to dominate the late stages of the race to take his second career NASCAR Winston Cup Series victory and his second victory of the season. To fill out the podium, Roush Racing driver Mark Martin and Joe Gibbs Racing driver Bobby Labonte would finish second and third, respectively.
The 1998 DieHard 500 was the ninth stock car race of the 1998 NASCAR Winston Cup Series season and the 29th iteration of the event. The race was held on Sunday, April 26, 1998, in Lincoln, Alabama at Talladega Superspeedway, a 2.66 miles permanent triangle-shaped superspeedway. The race took the scheduled 188 laps to complete. In the final laps of the race, Joe Gibbs Racing driver Bobby Labonte would make a pass on Terry Labonte with two to go and fend off the field to take his seventh career NASCAR Winston Cup Series victory and his second and final victory of the season. To fill out the podium, Travis Carter Enterprises driver Jimmy Spencer and Robert Yates Racing driver Dale Jarrett would finish second and third, respectively.
The 1998 MBNA Platinum 400 was the 12th stock car race of the 1998 NASCAR Winston Cup Series season and the 30th iteration of the event. The race was held on Sunday, May 31, 1998, 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. Within the final laps of the race, Robert Yates Racing driver Dale Jarrett would manage to save enough fuel and overtake the dominant driver of the race, Hendrick Motorsports driver Jeff Gordon to take his 17th career NASCAR Winston Cup Series victory and his second victory of the season. To fill out the podium, Roush Racing driver Jeff Burton and Jeff Gordon would finish second and third, respectively.
The 1998 Pontiac Excitement 400 was the 13th stock car race of the 1998 NASCAR Winston Cup Series season and the 44th iteration of the event. The race was held on Saturday, June 6, 1998, in Richmond, Virginia, at Richmond International Raceway, a 0.75 miles (1.21 km) D-shaped oval. The race took the scheduled 400 laps to complete. With two laps to go, Hendrick Motorsports driver Terry Labonte would make a final pass in a battle with Robert Yates Racing driver Dale Jarrett. On the fourth turn of the penultimate lap, the caution would come out for Johnny Benson Jr. Labonte was able to defend Jarrett and complete the penultimate lap to take his 20th career NASCAR Winston Cup Series victory and his only victory of the season. To fill out the podium, Jarrett and Penske-Kranefuss Racing driver Rusty Wallace would finish second and third, respectively. The event was overshadowed when Rusty Wallace completely took out Jeff Gordon in turn 2 with 29 laps to go. Gordon in his interview when asked what happened, he replied "well, that's pretty obvious you tell me you know. You got on video. I think it's pretty simple you know I uh- I had the position on him. He just drove into the left rear. I don't know what happened."
The 1998 Save Mart/Kragen 350 was the 16th stock car race of the 1998 NASCAR Winston Cup Series season and the 10th iteration of the event. The race was held on Sunday, June 28, 1998, in Sonoma, California, at the club layout in Sears Point Raceway, a 1.949 miles (3.137 km) permanent road course layout. The race took the scheduled 112 laps to complete. Hendrick Motorsports driver Jeff Gordon would lead a charge from 20th to the lead within the closing laps of the race to take his 33rd career NASCAR Winston Cup Series victory and his fourth of the season. To fill out the podium, Morgan–McClure Motorsports driver Bobby Hamilton and Petty Enterprises driver John Andretti would finish second and third, respectively.
The 1998 NAPA Autocare 500 was the 27th stock car race of the 1998 NASCAR Winston Cup Series season and the 50th iteration of the event. The race was held on Sunday, September 27, 1998, 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. Battling immense heat, Rudd Performance Motorsports driver Ricky Rudd would manage to dominate the late stages of the race to take his 20th career NASCAR Winston Cup Series victory and his only victory 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 1998 UAW-GM Quality 500 was the 28th stock car race of the 1998 NASCAR Winston Cup Series season and the 39th iteration of the event. The race was held on Sunday, October 4, 1998, 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. At race's end, Roush Racing driver Mark Martin would manage to dominate most of the race to take his 29th career NASCAR Winston Cup Series victory and his seventh and final victory of the season. To fill out the podium, Bill Davis Racing driver Ward Burton and Roush Racing driver Jeff Burton would finish second and third, respectively.
The 1998 Winston 500 was the 29th stock car race of the 1998 NASCAR Winston Cup Series season, the last of five races of that year's Winston No Bull 5, and the 29th iteration of the event. The race was held on Sunday, October 11, 1998, in Lincoln, Alabama at Talladega Superspeedway, a 2.66 miles permanent triangle-shaped superspeedway. The race took the scheduled 188 laps to complete. In the last 13 laps of the race, Robert Yates Racing driver Dale Jarrett would manage to defend the field to take his 18th career NASCAR Winston Cup Series victory, his third and final victory of the season, and a US$1,000,000 bonus for claiming the Winston No Bull 5 bonus. To fill out the top three, Jeff Gordon and Terry Labonte, both driving for Hendrick Motorsports, 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 2001 Virginia 500 was the eighth stock car race of the 2001 NASCAR Winston Cup Series and the 52nd iteration of the event. The race was held on Sunday, April 8, 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. Within the final laps of the race, Robert Yates Racing driver Dale Jarrett would manage to pass teammate Ricky Rudd to earn his 27th career NASCAR Winston Cup Series victory and his third victory of the season. To fill out the top three, Rudd and Roush Racing driver Jeff Burton 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 and his sixth victory of the season. 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.
