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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 (2.4 km) 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 All-Star Race 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.
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