The 1999 NASCAR Winston Cup Series was the 51st season of professional Stock car racing in the United States, the 28th modern-era Cup series, and the last Cup season of the 1990s and the 20th century. The season began on Sunday, February 7, and ended on Sunday, November 21. Dale Jarrett, representing Robert Yates Racing, was crowned the champion, while the NASCAR Manufacturers' Championship was won by the Ford drivers with 13 wins and 231 points over second-place Chevrolet who had 12 wins and 210 points and third place Pontiac who had 9 wins and 205 points.

In December 1999, NASCAR announced that starting in February 2001, the Winston Cup Series and Busch Grand National Series would be broadcast live on FOX/FX and NBC/TBS (later TNT).

Teams and drivers

Complete schedule ManufacturerTeamRace driverCrew chief ChevroletAndy Petree Racing33 Ken Schrader Sammy Johns55 Kenny Wallace Jimmy ElledgeDale Earnhardt, Inc.1 Steve Park Phillipe Lopez Steve Hmiel Paul Andrews Hendrick Motorsports5 Terry Labonte Andy Graves24 Jeff Gordon Ray Evernham Brian Whitesell 25 Wally Dallenbach Jr. Tony FurrJoe Bessey Motorsports60 Geoff Bodine Jim LongLarry Hedrick Motorsports41 David Green Tim Brewer Mike Hill Donnie Disharoon Dick Trickle Derrike Cope Gary Bradberry Marcis Auto Racing71 Dave Marcis Bob Marcis R. K. Smith Mattei Motorsports7 Michael Waltrip Bobby KennedyMorgan-McClure Motorsports4 Bobby Hamilton Charlie Pressley Gary DeHart Richard Childress Racing3 Dale Earnhardt Kevin Hamlin31 Mike Skinner Larry McReynoldsTeam SABCO40 Sterling Marlin Corrie Stott Tony Glover Scott Eggleston 42 Joe Nemechek Scott Eggleston Tony Glover FordElliott-Marino RacingBill Elliott Racing94 Bill Elliott Joe Garone Jerry Pitts Wayne Orme Ernie Elliott Brett Bodine Racing11 Brett Bodine Gere Kennon Rick Gay Butch Mock MotorsportsGalaxy Motorsports75 Ted Musgrave Jon Wolfe Greg Ely Hut Stricklin Yarborough Burdette Motorsports98 Rick Mast Michael McSwain Jerry Pitts Mark Tutor Dan Glauz Haas-Carter Motorsports23 Jimmy Spencer Donnie Wingo66 Darrell Waltrip Donnie Disharoon Joe Snyder Travis Carter Mark Tutor Phillippe Lopez Jasper Motorsports77 Robert Pressley Newt Moore Charley Pressley Melling Racing9 Jerry Nadeau Jeff Buice Newt Moore Kevin Cram Steve Grissom Rich Bickle Stacy Compton Penske-Kranefuss Racing2 Rusty Wallace Robin Pemberton12 Jeremy Mayfield Paul Andrews Peter Sospenzo Robert Yates Racing28 Kenny Irwin Jr. Doug Richert Ray Fox 88 Dale Jarrett Todd ParrottRoush Racing6 Mark Martin Jimmy Fennig16 Kevin Lepage James Ince Tommy Morgan Skip Eyler Pat Tryson 26 Johnny Benson Bobby Leslie Pat Tryson Tommy Morgan 97 Chad Little Jeff Hammond99 Jeff Burton Frank StoddardRudd Performance Motorsports10 Ricky Rudd Bill Ingle Dan Stillman Michael McSwain Wood Brothers Racing21 Elliott Sadler (R) Mike Beam PontiacBahari RacingEel River Racing30 Derrike Cope Dan Glauz Barry Dodson Todd Bodine Mike Bliss Buckshot Jones (R) Bill Davis Racing22 Ward Burton Tommy Baldwin Jr.Joe Gibbs Racing18 Bobby Labonte Jimmy Makar20 Tony Stewart (R) Greg ZipadelliMB2 Motorsports36 Ernie Irvan Ryan Pemberton Dick Trickle Jerry Nadeau Petty Enterprises43 John Andretti Robbie Loomis44 Kyle Petty Doug HewittTyler Jet Motorsports45 Rich Bickle Phil Hammer Bill Ingle James Ince Jack Sprague David Green

Limited schedule ManufacturerTeamRace driverCrew chiefRound(s) ChevroletBarkdoll Racing 73 Ken Bouchard Dale Earnhardt, Inc. 8 Dale Earnhardt Jr. Tony Eury Sr. Highland Timber Racing 08 Harris DeVane Fast Track Racing 48 Glen Morgan AC Motorsports89 Austin Cameron Gerhart Racing Bobby Gerhart LJ Racing 91 Steve Grissom Skip Eyler Joe Falk Nicholas Short Dick Trickle Hut Stricklin Morgan Shepherd Jack Baldwin Tom Baldwin Derrike Cope Tim Fedewa Andy Hillenburg Rich Bickle Marcis Auto Racing 72 Jim Sauter Ted Christopher Racing 13 Ted Christopher Kevin Cram Metcalf Motorsports 70 John Metcalf Midwest Transit Racing 50 Dan Pardus (R) John McQueen Jay Born John Monsam Billy Standridge Ron Hornaday Jr. Ricky Craven NEMCO Motorsports 87 Ron Fellows Brian Pattie Petty-Huggins Racing 84 Stanton Barrett (R) Ken Bouchard Team SABCO 01 Jeff Green Bob Temple Steve Grissom Ron Hornaday Jr. T.R.I.X. Racing 79 Norm Benning Ted Walters Andy Belmont FordElliott-Marino Racing 13 Dick Trickle Wayne Orme Bud Moore EngineeringFenley-Moore Motorsports 15 Jeff Green Derrike Cope 62 Lance Hooper CSG Racing 59 Mark Gibson Tony Gibson Zali Racing 92 Morgan Shepherd Brian Bass Donlavey Racing 90 Mike Wallace Greg Connor Junie Donlavey Mike Harmon (R) Morgan Shepherd Stanton Barrett (R) Ed Berrier Loy Allen Jr. Hut Stricklin Hover Motorsports 80 Andy Hillenburg Gary Bradberry Irvan-Simo Racing 14 Randy LaJoie Jerry Baxter Boris Said Buckshot Jones (R) Jenn West Motorsports 38 Butch Gilliland Mansion Motorsports 85 Carl Long Meacham Racing 04 Andy Belmont Phoenix Air Racing 61 David Murry Bob Bissinger Bob Strait Donnie Straight Pinnacle Motorsports 81 Morgan Shepherd Roehrig Motorsports 19 Tom Hubert Mike Bodick Ron Burns Racing 68 Ron Burns Roush Racing 17 Matt Kenseth Robbie Reiser SBIII Motorsports 58 Ricky Craven Mike Hillman Jerry Pitts Loy Allen Jr. Sean Woodside Hut Stricklin Standridge Motorsports 47 Billy Standridge Dave Smith Triad Motorsports 78 Gary Bradberry Hut Stricklin Ultra Motorsports 32 Mike Wallace Tim Brewer PontiacBill Davis Racing 93 Dave Blaney Gil Martin Buckshot Racing 00 Buckshot Jones (R) Tony Barclay Shepherd Racing 05 Morgan Shepherd Golden Gate Racing Team 96 Steve Portenga Joyner-Kersee Racing 19 Tom Hubert Mike Bodick Paul Gentilozzi Midgley Motorsports 09 Mike Borkowski

Mike Harmon was released just before the Daytona 500 and never drove or attempted any of the races in 1999.

Schedule No. Race title Track DateBud Shootout QualifierDaytona International Speedway, Daytona BeachFebruary 7Bud ShootoutGatorade 125sFebruary 111Daytona 500February 142Dura Lube/Big K 400North Carolina Speedway, RockinghamFebruary 213Las Vegas 400Las Vegas Motor Speedway, Las VegasMarch 74Cracker Barrel 500Atlanta Motor Speedway, HamptonMarch 145TranSouth Financial 400Darlington Raceway, DarlingtonMarch 216Primestar 500Texas Motor Speedway, Fort WorthMarch 287Food City 500Bristol Motor Speedway, BristolApril 118Goody's Body Pain 500Martinsville Speedway, RidgewayApril 189DieHard 500Talladega Superspeedway, TalladegaApril 2510California 500 presented by NAPACalifornia Speedway, FontanaMay 211Pontiac Excitement 400Richmond International Raceway, RichmondMay 15No Bull 25 ShootoutLowe's Motor Speedway, ConcordMay 22Winston OpenThe Winston12Coca-Cola 600May 3013MBNA Platinum 400Dover Downs International Speedway, DoverJune 614Kmart 400Michigan Speedway, BrooklynJune 1315Pocono 500Pocono Raceway, Long PondJune 2016Save Mart/Kragen 350Sears Point Raceway, SonomaJune 2717Pepsi 400Daytona International Speedway, Daytona BeachJuly 318Jiffy Lube 300New Hampshire International Speedway, LoudonJuly 1119Pennsylvania 500Pocono Raceway, Long PondJuly 2520Brickyard 400Indianapolis Motor Speedway, SpeedwayAugust 721Frontier at The GlenWatkins Glen International, Watkins GlenAugust 1522Pepsi 400 presented by MeijerMichigan Speedway, BrooklynAugust 2223Goody's Headache Powder 500Bristol Motor Speedway, BristolAugust 2824The 50th Pepsi Southern 500Darlington Raceway, DarlingtonSeptember 525Exide NASCAR Select Batteries 400Richmond International Raceway, RichmondSeptember 1126Dura Lube/Kmart 300New Hampshire International Speedway, LoudonSeptember 1927MBNA Gold 400Dover Downs International Speedway, DoverSeptember 2628NAPA Autocare 500Martinsville Speedway, RidgewayOctober 329UAW-GM Quality 500Lowe's Motor Speedway, ConcordOctober 1130Winston 500Talladega Superspeedway, TalladegaOctober 1731Pop Secret Microwave Popcorn 400North Carolina Speedway, RockinghamOctober 2432Checker Auto Parts/Dura Lube 500Phoenix International Raceway, PhoenixNovember 733Pennzoil 400 presented by KmartHomestead-Miami Speedway, HomesteadNovember 1434NAPA 500Atlanta Motor Speedway, HamptonNovember 21

Races No.RacePole positionMost laps ledWinning driverBud Shootout QualifierGeoff BodineMike SkinnerMike SkinnerChevroletBud ShootoutRusty WallaceMark MartinMark MartinFordGatorade 125 No. 1Jeff GordonJeff GordonBobby LabontePontiacGatorade 125 No. 2Tony StewartDale EarnhardtDale EarnhardtChevrolet1Daytona 500Jeff GordonRusty WallaceJeff GordonChevrolet2Dura Lube/Big K 400Ricky RuddJeff BurtonMark MartinFord3Las Vegas 400Bobby LabonteJeff BurtonJeff BurtonFord4Cracker Barrel 500Bobby LabonteJeff GordonJeff GordonChevrolet5TranSouth Financial 400Jeff GordonJeff BurtonJeff BurtonFord6Primestar 500Kenny Irwin Jr.Terry LabonteTerry LabonteChevrolet7Food City 500Rusty WallaceRusty WallaceRusty WallaceFord8Goody's Body Pain 500Tony StewartRusty WallaceJohn AndrettiPontiac9DieHard 500Ken SchraderDale EarnhardtDale EarnhardtChevrolet10California 500 pres. by NAPAJeff BurtonJeff GordonJeff GordonChevrolet11Pontiac Excitement 400Jeff GordonJeff BurtonDale JarrettFordNo Bull 25 Race 1Steve ParkMike SkinnerMike SkinnerChevroletNo Bull 25 Race 2Tony StewartTony StewartTony StewartPontiacWinston OpenMike SkinnerTony StewartTony StewartPontiacThe WinstonBobby LabonteJeff GordonTerry LabonteChevrolet12Coca-Cola 600Bobby LabonteJeff BurtonJeff BurtonFord13MBNA Platinum 400Bobby LabonteTony StewartBobby LabontePontiac14Kmart 400 pres. by Castrol Super CleanJeff GordonDale JarrettDale JarrettFord15Pocono 500Sterling MarlinDale JarrettBobby LabontePontiac16Save Mart/Kragen 350Jeff GordonJeff GordonJeff GordonChevrolet17Pepsi 400Joe NemechekRusty WallaceDale JarrettFord18Jiffy Lube 300Jeff GordonTony StewartJeff BurtonFord19Pennsylvania 500Mike SkinnerMike SkinnerBobby LabontePontiac20Brickyard 400Jeff GordonDale JarrettDale JarrettFord21Frontier at the GlenRusty WallaceJeff GordonJeff GordonChevrolet22Pepsi 400 pres. by MeijerWard BurtonJeff GordonBobby LabontePontiac23Goody's Headache Powder 500Tony StewartTony StewartDale EarnhardtChevrolet24The 50th Pepsi Southern 500Kenny Irwin Jr.Jeff BurtonJeff BurtonFord25Exide NASCAR Select Batteries 400Mike SkinnerTony StewartTony StewartPontiac26Dura Lube/Kmart 300Rusty WallaceRusty WallaceJoe NemechekChevrolet27MBNA Gold 400Rusty WallaceMark MartinMark MartinFord28NAPA Autocare 500Joe NemechekMike SkinnerJeff GordonChevrolet29UAW-GM Quality 500Bobby LabonteBobby LabonteJeff GordonChevrolet30Winston 500Joe NemechekJeff GordonDale EarnhardtChevrolet31Pop Secret Microwave Popcorn 400Mark MartinDale JarrettJeff BurtonFord32Checker Auto Parts/Dura Lube 500John AndrettiTony StewartTony StewartPontiac33Pennzoil 400 pres. by KmartDavid GreenBobby LabonteTony StewartPontiac34NAPA 500Kevin LepageBobby LabonteBobby LabontePontiac

Bud Shootout The Bud Shootout, an exhibition race for drivers who had won a pole position in the previous season or had won the event before, was held on February 7 at Daytona International Speedway. The starting grid was decided by random draw. Rusty Wallace drew the pole.

Top ten results

#6 - Mark Martin #33 - Ken Schrader #18 - Bobby Labonte #31 - Mike Skinner #12 - Jeremy Mayfield #22 - Ward Burton #2 - Rusty Wallace #88 - Dale Jarrett #98 - Rick Mast #28 - Kenny Irwin Jr.

Gatorade Twin 125s The Gatorade Twin 125s, a pair of qualifying races for the Daytona 500, were held February 11 at Daytona International Speedway. Jeff Gordon and Tony Stewart won the pole positions for the races, respectively.

Race one: top ten results #18 - Bobby Labonte #24 - Jeff Gordon #99 - Jeff Burton #33 - Ken Schrader #6 - Mark Martin #26 - Jimmy Spencer #7 - Michael Waltrip #77 - Robert Pressley #40 - Sterling Marlin #5 - Terry Labonte

Race two: top ten results #3 - Dale Earnhardt* #12 - Jeremy Mayfield #88 - Dale Jarrett #2 - Rusty Wallace #31 - Mike Skinner #20 - Tony Stewart #16 - Kevin Lepage #4 - Bobby Hamilton #22 - Ward Burton #30 - Derrike Cope