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 Pontiac Excitement 400 was the 11th stock car race of the 2000 NASCAR Winston Cup Series and the 46th iteration of the event. The race was held on Saturday, May 6, 2000, 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. At race's end, Dale Earnhardt Jr., driving for Dale Earnhardt, Inc., would hold onto the lead after making a four-tire call on the final round of pit stops to win his second career NASCAR Winston Cup Series win and his second and final win of the season. To fill out the podium, Terry Labonte of Hendrick Motorsports and Dale Jarrett of Robert Yates Racing would finish second and third, respectively.
The 2000 Kmart 400 was the 14th stock car race of the 2000 NASCAR Winston Cup Series and the 32nd iteration of the event. The race was held on Sunday, June 11, 2000, in Brooklyn, Michigan, at Michigan International Speedway, a two-mile moderate-banked D-shaped speedway. The race was shortened from its scheduled 200 laps to 194 due to inclement weather. At race's end, Tony Stewart, driving for Joe Gibbs Racing, would manage to hold off the field until lap 193 when the race was stopped for rain. The win was Stewart's fifth career NASCAR Winston Cup Series win and his second of the season. To fill out the podium, Dale Earnhardt of Richard Childress Racing and Bobby Labonte of Joe Gibbs Racing would finish second and third, respectively.
The 2001 Pontiac Excitement 400 was the 11th stock car race of the 2001 NASCAR Winston Cup Series and the 47th iteration of the event. The race was held on Saturday, May 5, 2001, 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. At race's end, Tony Stewart, driving for Joe Gibbs Racing, would hold off the field on the final restart with two to go to win his 10th career NASCAR Winston Cup Series win and his first of the season. To fill out the podium, Jeff Gordon, driving for Hendrick Motorsports, and Rusty Wallace, driving for Penske Racing South, would finish second and third, respectively.
The 2001 Kmart 400 was the 14th stock car race of the 2001 NASCAR Winston Cup Series and the 33rd iteration of the event. The race was held on Sunday, June 10, 2001, 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, Jeff Gordon, driving for Hendrick Motorsports, would manage to hold off the field on the final restart with four to go to win his 55th career NASCAR Winston Cup Series win and his third of the season. The win was also Hendrick Motorsports' 100th NASCAR Winston Cup Series victory. To fill out the podium, Ricky Rudd, driving for Robert Yates Racing, and Sterling Marlin, driving for Chip Ganassi Racing with Felix Sabates, would finish second and third, respectively.
The 2001 New England 300 was the 19th stock car race of the 2001 NASCAR Winston Cup Series and the ninth iteration of the event. The race was held on Sunday, July 22, 2001, in Loudon, New Hampshire, at New Hampshire International Speedway, a 1.058-mile (1.703 km) permanent, oval-shaped, low-banked racetrack. The race took the scheduled 300 laps to complete. On the final restart with five to go, Dale Jarrett, driving for Robert Yates Racing, would perform a bump-and-run on teammate Ricky Rudd to pull away and win his 29th career NASCAR Winston Cup Series win and his fourth and final win of the season. Rudd was credited with a third-place finish. To fill out the podium, Jeff Gordon, driving for Hendrick Motorsports, would finish second.
The 2001 Pennsylvania 500 presented by Pep Boys was the 20th stock car race of the 2001 NASCAR Winston Cup Series and the 29th iteration of the event. The race was held on Sunday, July 29, 2001, 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 laps of the race, Bobby Labonte, driving for Joe Gibbs Racing, would pass eventual second-place driver, Dale Earnhardt, Inc. driver Dale Earnhardt Jr. to win his 17th career NASCAR Winston Cup Series win and his first of the season. To fill out the podium, Tony Stewart, driving for Joe Gibbs Racing, would finish third.
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 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 1998 Goody's Headache Powder 500 was the eighth stock car race of the 1998 NASCAR Winston Cup Series season and the 49th iteration of the event. The race was originally scheduled to be held on Sunday, April 19, 1998, but was postponed to Monday, April 20, due to rain. The race was held 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, Morgan–McClure Motorsports driver Bobby Hamilton would manage to dominate not only the race, but most of the race weekend to take his third career NASCAR Winston Cup Series victory and his only victory of the season. The win also marked the final Winston Cup victory for Morgan–McClure Motorsports. To fill out the podium, Roush Racing driver Ted Musgrave and Robert Yates Racing driver Dale Jarrett would finish second and third, respectively.
The 1998 Exide NASCAR Select Batteries 400 was the 25th stock car race of the 1998 NASCAR Winston Cup Series season and the 41st iteration of the event. The race was held on Saturday, September 12, 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. In a close finish, Roush Racing driver Jeff Burton was able to fend off Hendrick Motorsports driver Jeff Gordon at the line by 0.051 seconds to win his fifth career NASCAR Winston Cup Series and his second and final victory of the season. To fill out the podium, Roush Racing driver Mark Martin would finish third.
The 1998 MBNA Gold 400 was the 26th stock car race of the 1998 NASCAR Winston Cup Series season and the 30th iteration of the event. The race was held on Sunday, September 20, 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. At race's end, Roush Racing driver Mark Martin would dominate the race weekend to take his 28th career NASCAR Winston Cup Series victory and his sixth victory of the season. To fill out the podium, Hendrick Motorsports driver Jeff Gordon and Penske-Kranefuss Racing driver Jeremy Mayfield would finish second and third, respectively.
The 1998 Dura Lube/Kmart 500 was the 31st stock car race of the 1998 NASCAR Winston Cup Series season and the 11th iteration of the event. The race was held on Sunday, October 25, 1998, in Avondale, Arizona at Phoenix International Raceway, a 1-mile (1.6 km) permanent low-banked tri-oval race track. The race was shortened from its scheduled 312 laps to 257 laps due to inclement weather. At race's end, Penske-Kranefuss Racing driver Rusty Wallace would dominate the race when the race was stopped to take his 48th career NASCAR Winston Cup Series victory and his only victory of the season. To fill out the podium, Roush Racing driver Mark Martin and Richard Childress Racing driver Dale Earnhardt would finish second and third, respectively.
The 2003 MBNA Armed Forces Family 400 was the 13th stock car race of the 2003 NASCAR Winston Cup Series season and the 35th iteration of the event. The race was held on Sunday, June 1, 2003, 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. At race's end, Penske Racing South driver Ryan Newman would manage to dominate the late stages of the race to take his third career NASCAR Winston Cup Series victory and his second victory of the season. To fill out the top 3, Hendrick Motorsports driver Jeff Gordon 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 2003 Checker Auto Parts 500 presented by Havoline was the 34th stock car race of the 2003 NASCAR Winston Cup Series season and the 16th iteration of the event. The race was held on Sunday, November 2, 2003, before an audience of 100,000 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. Within the final laps of the race, Dale Earnhardt, Inc. driver Dale Earnhardt Jr. would manage to defend the field on the final restart with nine to go to take his ninth career NASCAR Winston Cup Series victory and his second and final victory of the season. To fill out the top three, Hendrick Motorsports driver Jimmie Johnson and Penske Racing South driver Ryan Newman 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 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.
