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.