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. 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.

#DriverTeamMake1Steve ParkDale Earnhardt, Inc.Chevrolet2Rusty WallacePenske-Kranefuss RacingFord3Dale EarnhardtRichard Childress RacingChevrolet4Bobby HamiltonMorgan–McClure MotorsportsChevrolet5Terry LabonteHendrick MotorsportsChevrolet6Mark MartinRoush RacingFord7Michael WaltripMattei MotorsportsChevrolet9Jerry NadeauMelling RacingFord10Ricky RuddRudd Performance MotorsportsFord11Brett BodineBrett Bodine RacingFord12Jeremy MayfieldPenske-Kranefuss RacingFord16Kevin LepageRoush RacingFord18Bobby LabonteJoe Gibbs RacingPontiac20Tony StewartJoe Gibbs RacingPontiac21Elliott SadlerWood Brothers RacingFord22Ward BurtonBill Davis RacingPontiac23Jimmy SpencerHaas-Carter MotorsportsFord24Jeff GordonHendrick MotorsportsChevrolet25Wally Dallenbach Jr.Hendrick MotorsportsChevrolet26Johnny Benson Jr.Roush RacingFord28Kenny Irwin Jr.Robert Yates RacingFord30Derrike CopeBahari RacingPontiac31Mike SkinnerRichard Childress RacingChevrolet33Ken SchraderAndy Petree RacingChevrolet36Ernie IrvanMB2 MotorsportsPontiac40Sterling MarlinTeam SABCOChevrolet41David GreenLarry Hedrick MotorsportsChevrolet42Joe NemechekTeam SABCOChevrolet43John AndrettiPetty EnterprisesPontiac44Kyle PettyPetty EnterprisesPontiac45Rich BickleTyler Jet MotorsportsPontiac55Kenny WallaceAndy Petree RacingChevrolet58Hut StricklinSBIII MotorsportsFord60Geoff BodineJoe Bessey RacingChevrolet66Darrell WaltripHaas-Carter MotorsportsFord71Dave MarcisMarcis Auto RacingChevrolet75Ted MusgraveButch Mock MotorsportsFord77Robert PressleyJasper MotorsportsFord88Dale JarrettRobert Yates RacingFord90Stanton BarrettDonlavey RacingFord91Morgan ShepherdLJ RacingChevrolet94Bill ElliottBill Elliott RacingFord97Chad LittleRoush RacingFord98Rick MastCale Yarborough MotorsportsFord99Jeff BurtonRoush RacingFordOfficial entry list

Practice

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 . Pos.#DriverTeamMakeTimeSpeed140Sterling MarlinTeam SABCOChevrolet53.445168.397242Joe NemechekTeam SABCOChevrolet53.516168.174324Jeff GordonHendrick MotorsportsChevrolet53.562168.030Full second practice results

Second practice The second practice session was held on Friday, July 23, at 10:35a.m. 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 . Pos.#DriverTeamMakeTimeSpeed140Sterling MarlinTeam SABCOChevrolet53.007169.78826Mark MartinRoush RacingFord53.033169.705324Jeff GordonHendrick MotorsportsChevrolet53.109169.462Full first practice results

Third practice The third practice session was held on Saturday, July 24, at 9:30a.m. 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 .

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. Pos.#DriverTeamMakeTimeSpeed141David GreenLarry Hedrick MotorsportsChevrolet53.806167.267288Dale JarrettRobert Yates RacingFord53.824167.211310Ricky RuddRudd Performance MotorsportsFord53.862167.093Full second practice results

Final practice The final practice session, sometimes referred to as Happy Hour, was held on Saturday, July 24. 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 . Pos.#DriverTeamMakeTimeSpeed122Ward BurtonBill Davis RacingPontiac54.380165.50226Mark MartinRoush RacingFord54.399165.444312Jeremy MayfieldPenske-Kranefuss RacingFord54.434165.337Full Happy Hour practice results

Qualifying Qualifying was split into two rounds. The first round was held on Friday, July 23, at 3:00p.m. 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 11:30a.m. 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 .

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

Full qualifying results Pos.#DriverTeamMakeTimeSpeed131Mike SkinnerRichard Childress RacingChevrolet52.801170.45126Mark MartinRoush RacingFord52.917170.078333Ken SchraderAndy Petree RacingChevrolet52.962169.933418Bobby LabonteJoe Gibbs RacingPontiac52.995169.827543John AndrettiPetty EnterprisesPontiac53.008169.786625Wally Dallenbach Jr.Hendrick MotorsportsChevrolet53.089169.527724Jeff GordonHendrick MotorsportsChevrolet53.092169.517822Ward BurtonBill Davis RacingPontiac53.112169.453940Sterling MarlinTeam SABCOChevrolet53.115169.4441042Joe NemechekTeam SABCOChevrolet53.129169.399113Dale EarnhardtRichard Childress RacingChevrolet53.222169.1031220Tony Stewart (R)Joe Gibbs RacingPontiac53.231169.0741345Rich BickleTyler Jet MotorsportsPontiac53.236169.059145Terry LabonteHendrick MotorsportsChevrolet53.283168.9091588Dale JarrettRobert Yates RacingFord53.296168.868167Michael WaltripMattei MotorsportsChevrolet53.320168.792172Rusty WallacePenske-Kranefuss RacingFord53.321168.7891899Jeff BurtonRoush RacingFord53.330168.7611928Kenny Irwin Jr.Robert Yates RacingFord53.376168.6152012Jeremy MayfieldPenske-Kranefuss RacingFord53.389168.5742123Jimmy SpencerHaas-Carter MotorsportsFord53.447168.3912298Rick MastCale Yarborough MotorsportsFord53.447168.3912375Ted MusgraveButch Mock MotorsportsFord53.472168.3122436Ernie IrvanMB2 MotorsportsPontiac53.625167.8322571Dave MarcisMarcis Auto RacingChevrolet53.636167.7982611Brett BodineBrett Bodine RacingFord53.650167.754274Bobby HamiltonMorgan–McClure MotorsportsChevrolet53.663167.7132855Kenny WallaceAndy Petree RacingChevrolet53.687167.6382958Hut StricklinSBIII MotorsportsFord53.707167.5763090Stanton BarrettDonlavey RacingFord53.721167.5323116Kevin LepageRoush RacingFord53.728167.510321Steve ParkDale Earnhardt, Inc.Chevrolet53.732167.4983377Robert PressleyJasper MotorsportsFord53.736167.4853426Johnny Benson Jr.Roush RacingFord53.740167.4733510Ricky RuddRudd Performance MotorsportsFord53.749167.4453641David GreenLarry Hedrick MotorsportsChevrolet53.778167.355Provisionals3794Bill ElliottBill Elliott RacingFord -* -*3897Chad LittleRoush RacingFord -* -*3944Kyle PettyPetty EnterprisesPontiac -* -*4021Elliott Sadler (R)Wood Brothers RacingFord -* -*419Jerry NadeauMelling RacingFord -* -*4260Geoff BodineJoe Bessey RacingChevrolet -* -*Champion's Provisional4366Darrell WaltripHaas-Carter MotorsportsFord -* -*Failed to qualify4430Derrike CopeBahari RacingPontiac53.925166.8984591Morgan ShepherdLJ RacingChevrolet53.951166.818Official first round qualifying resultsOfficial starting lineup *Time not available.

Race results