1999 Pennsylvania 500

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.

Background
The race was held at Pocono Raceway, which is a three-turn superspeedway located in Long Pond, Pennsylvania. The track hosts two annual NASCAR Sprint Cup Series races, as well as one Xfinity Series and Camping World Truck Series event. Until 2019, the track also hosted an IndyCar Series race.

Pocono Raceway is one of a very few NASCAR tracks not owned by either Speedway Motorsports, Inc. or International Speedway Corporation. It is operated by the Igdalsky siblings Brandon, Nicholas, and sister Ashley, and cousins Joseph IV and Chase Mattioli, all of whom are third-generation members of the family-owned Mattco Inc, started by Joseph II and Rose Mattioli.

Outside of the NASCAR races, the track is used throughout the year by Sports Car Club of America (SCCA) and motorcycle clubs as well as racing schools and an IndyCar race. The triangular oval also has three separate infield sections of racetrack – North Course, East Course and South Course. Each of these infield sections use a separate portion of the tri-oval to complete the track. During regular non-race weekends, multiple clubs can use the track by running on different infield sections. Also some of the infield sections can be run in either direction, or multiple infield sections can be put together – such as running the North Course and the South Course and using the tri-oval to connect the two.

Entry list

 * (R) denotes rookie driver.

First practice
The second practice session was held on Friday, July 23. Sterling Marlin, driving for Team SABCO, would set the fastest time in the session, with a lap of 53.445 and an average speed of 168.397 mph.

Second practice
The second practice session was held on Friday, July 23, at 10:35 AM EST. The session would last for three hours and 25 minutes. Sterling Marlin, driving for Team SABCO, would set the fastest time in the session, with a lap of 53.007 and an average speed of 169.788 mph.

Third practice
The third practice session was held on Saturday, July 24, at 9:30 AM EST. The session would last for one hour and 20 minutes. David Green, driving for Larry Hedrick Motorsports, would set the fastest time in the session, with a lap of 53.806 and an average speed of 167.267 mph.

During the session, Wood Brothers Racing driver Elliott Sadler was involved in a wreck that resulted in an injured left foot. Despite fellow Morgan Shepherd being on standby for Sadler, Sadler would start the race.

Final practice
The final practice session, sometimes referred to as Happy Hour, was held on Saturday, July 24, after the preliminary 1999 Pepsi ARCA 200. The session would last for one hour. Ward Burton, driving for Bill Davis Racing, would set the fastest time in the session, with a lap of 54.380 and an average speed of 165.502 mph.

Qualifying
Qualifying was split into two rounds. The first round was held on Friday, July 23, at 3:00 PM EST. Each driver would have one lap to set a time. During the first round, the top 25 drivers in the round would be guaranteed a starting spot in the race. If a driver was not able to guarantee a spot in the first round, they had the option to scrub their time from the first round and try and run a faster lap time in a second round qualifying run, held on Saturday, July 24, at 11:30 AM EST. As with the first round, each driver would have one lap to set a time. Positions 26-36 would be decided on time, while positions 37-43 would be based on provisionals. Six spots are awarded by the use of provisionals based on owner's points. The seventh is awarded to a past champion who has not otherwise qualified for the race. If no past champion needs the provisional, the next team in the owner points will be awarded a provisional.

Mike Skinner, driving for Richard Childress Racing, would win the pole, setting a time of 52.801 and an average speed of 170.451 mph.

Two drivers would fail to qualify: Derrike Cope and Morgan Shepherd.

Full qualifying results
* Time not available.