1999 NASCAR Winston Cup Series

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.
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.
1999 was the last season before Kurt Busch and Ryan Newman joins as NASCAR drivers.

Teams and drivers

Complete schedule

Limited schedule

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

Races

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. 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

Dale Earnhardt wins his 12th Gatorade 125 at Daytona, an all-time record. Earnhardt also wins his 10th straight Gatorade 125, another NASCAR record. With his 10th straight victory, Earnhardt won every Gatorade 125 event of the 1990s, becoming the only driver in NASCAR history to win an event for an entire decade. This would also be Dale Earnhardt's final career Daytona NASCAR win.
Daytona 500

The 1999 Daytona 500 was held February 14 at Daytona International Speedway. Jeff Gordon won the pole. In winning the race as well, he became the first Daytona 500 pole sitter to win the race since Bill Elliott in 1987. This race is known for Gordon's daring three-wide pass on Rusty Wallace and Mike Skinner. Gordon passed Wallace after ducking to the apron, nearly plowing into the damaged car of Ricky Rudd. Skinner jumped to the outside and they raced three-wide for three laps until Dale Earnhardt gave Gordon the needed push. The race was also known for a determined Dale Earnhardt repeatedly trying to pass Jeff Gordon for the lead on the final lap, but Gordon beat Earnhardt to the finish. The race was also marked by a large crash on lap 135 in turn 3 that collected 13 cars and saw Dale Jarrett flip over twice.

24-Jeff Gordon
3-Dale Earnhardt
28-Kenny Irwin Jr.
31-Mike Skinner
7-Michael Waltrip
33-Ken Schrader
44-Kyle Petty
2-Rusty Wallace
97-Chad Little
98-Rick Mast

Failed to qualify: 50-Dan Pardus*, 59-Mark Gibson, 72-Jim Sauter, 48-Glen Morgan, 81-Morgan Shepherd, 78-Gary Bradberry, 73-Ken Bouchard, 15-Jeff Green, 80-Andy Hillenburg, 84-Stanton Barrett, 47-Billy Standridge, 41-David Green, 00-Buckshot Jones*, 91-Steve Grissom, 13-Dick Trickle, and 79-Norm Benning.

This would be the 3rd and final time in his career that Jeff Gordon would win 3 straight NASCAR races.
This was the first Winston No Bull 5 race of the season. Jeff Gordon won the million-dollar bonus.
This was Jeff Gordon's 2nd Daytona 500 win in 3 years.
This was the first Winston Cup race for future Cup champion Tony Stewart.
Dura Lube/Big K 400

The Dura Lube/Big K 400 was held February 21 at North Carolina Speedway. Ricky Rudd won the pole.
Top ten results

6-Mark Martin
88-Dale Jarrett
18-Bobby Labonte
99-Jeff Burton
12-Jeremy Mayfield
31-Mike Skinner
5-Terry Labonte
60-Geoffrey Bodine
4-Bobby Hamilton
2-Rusty Wallace

Failed to qualify: Derrike Cope, Buckshot Jones, Billy Standridge, Rich Bickle

Jeff Gordon lost his bid at another 4 straight victories, and for the first time since the previous June Richmond race, Gordon failed to finish in the top 10. He would finish the race in 39th due to a blown engine, and he would fall from 1st to 11th in points.
Las Vegas 400

The Las Vegas 400 was held March 7 at Las Vegas Motor Speedway. Bobby Labonte won the pole. The Burton brothers, Jeff and Ward, both led for a combined 182 of the race's 267 laps. In the end, after a great battle for the lead in the race's closing moments, Jeff would pass brother Ward and hold on for the win.
Top ten results

99-Jeff Burton
22-Ward Burton
24-Jeff Gordon
31-Mike Skinner
18-Bobby Labonte
36-Ernie Irvan
3-Dale Earnhardt
5-Terry Labonte
2-Rusty Wallace
6-Mark Martin

Failed to qualify: Ted Musgrave, Kyle Petty, Robert Pressley, Ron Hornaday Jr., Butch Gilliland, Dave Marcis, Morgan Shepherd, Ron Burns, Austin Cameron

This was the second Winston No Bull 5 race for 1999.
Cracker Barrel 500

The Cracker Barrel 500 was held March 14 at Atlanta Motor Speedway. Bobby Labonte won the pole.
Top ten results

24-Jeff Gordon
18-Bobby Labonte
6-Mark Martin
99-Jeff Burton
88-Dale Jarrett
31-Mike Skinner
36-Ernie Irvan
22-Ward Burton
97-Chad Little
7-Michael Waltrip

Failed to qualify: Robert Pressley, Steve Grissom, Morgan Shepherd, Harris DeVane

TranSouth Financial 400

The TranSouth Financial 400 was held March 21 at Darlington Raceway. Jeff Gordon won the pole. The race was halted on lap 164 due to rain and never resumed. Jeff Burton was involved in a multi-car wreck that occurred just as the rain started pouring, but managed to limp across the start/finish line to take the win. Jeff Gordon was running 2nd before being passed by Jeremy Mayfield after being involved in the same wreck. Gordon still finished 3rd. Prior to the race, Bobby Labonte injured his shoulder in a practice crash. Bobby started the race, but on the first pit stop, Matt Kenseth relieved Labonte and would go on to finish 10th.
Top ten results

99-Jeff Burton
12-Jeremy Mayfield
24-Jeff Gordon
88-Dale Jarrett
6-Mark Martin
20-Tony Stewart
4-Bobby Hamilton
22-Ward Burton
43-John Andretti
18-Bobby Labonte

Failed to qualify: Derrike Cope, Dave Marcis, Rich Bickle

First career top-10 for Tony Stewart.
Primestar 500

The Primestar 500 was held March 28 at Texas Motor Speedway. Kenny Irwin Jr. won the pole.
Top ten results

5-Terry Labonte
88-Dale Jarrett
18-Bobby Labonte
2-Rusty Wallace
12-Jeremy Mayfield
20-Tony Stewart
99-Jeff Burton
3-Dale Earnhardt
40-Sterling Marlin
21-Elliott Sadler

Failed to qualify: Dick Trickle, Stanton Barrett, Kyle Petty, Dave Marcis, Ken Bouchard

This race would end under the caution flag as with just a couple laps to go Jimmy Spencer was involved in an accident, bringing out the yellow flag.
This race was notable for Terry Labonte claiming a home state victory. This would be Terry's last win until the 2003 Southern 500 at Darlington, 4 years and 157 races later.
This race would be the first and only time in his career that Jeff Gordon finished last in a 43-car field.
Food City 500

The Food City 500 was held April 11 at Bristol Motor Speedway. Rusty Wallace won the pole.
Top ten results

2-Rusty Wallace
6-Mark Martin
88-Dale Jarrett
43-John Andretti
99-Jeff Burton
24-Jeff Gordon
75-Ted Musgrave
44-Kyle Petty
22-Ward Burton
3-Dale Earnhardt

Failed to qualify: Rich Bickle, Stanton Barrett, Derrike Cope, Carl Long

Rusty Wallace led 425 of the 500 laps on his way to a dominating victory. This was Wallace's 49th career win, putting him 10th on the NASCAR all time win list.
Jeff Gordon was involved in a multi-car crash with about 50 laps left, but because so few cars were left on the lead lap, Gordon was able to rally to a sixth-place finish.
Goody's Body Pain 500

The Goody's Body Pain 500 was held on April 18 at Martinsville Speedway. Tony Stewart won the pole.
Top ten results

43-John Andretti
99-Jeff Burton
24-Jeff Gordon
31-Mike Skinner
6-Mark Martin
55-Kenny Wallace
2-Rusty Wallace
88-Dale Jarrett
33-Ken Schrader
44-Kyle Petty

Failed to qualify: Dave Marcis, Morgan Shepherd, Buckshot Jones

This was the last time until the 2014 Coke Zero 400 that the famous 43 car visited victory lane in a Cup Series race
Last win for John Andretti and Petty Enterprises.
First career Pole for Tony Stewart.
DieHard 500

The DieHard 500 was held April 25 at Talladega Superspeedway. Ken Schrader won the pole.
Top ten results

3 -Dale Earnhardt
88-Dale Jarrett
6 -Mark Martin
18-Bobby Labonte
20-Tony Stewart
33-Ken Schrader
55-Kenny Wallace
9 -Jerry Nadeau
43-John Andretti
94-Bill Elliott

Failed to qualify: Ken Bouchard, Dan Pardus, Derrike Cope, Loy Allen Jr., Dick Trickle

First career top-5 for Tony Stewart.
California 500 Presented by NAPA

The California 500 presented by NAPA was held May 2 at California Speedway. Since qualifying was rained out the lineup was set by owner's points, and Jeff Burton started on the pole.
Top ten results

24-Jeff Gordon
99-Jeff Burton
18-Bobby Labonte
20-Tony Stewart
88-Dale Jarrett
22-Ward Burton
12-Jeremy Mayfield
25-Wally Dallenbach Jr.
5-Terry Labonte
31-Mike Skinner 1 lap down

Failed to qualify: Boris Said, Hut Stricklin, Buckshot Jones, Butch Gilliland

Pontiac Excitement 400

The Pontiac Excitement 400 was held May 15 at Richmond International Raceway. Jeff Gordon won the pole.
Top ten results

88-Dale Jarrett
6-Mark Martin
18-Bobby Labonte
4-Bobby Hamilton
2-Rusty Wallace
42-Joe Nemechek
44-Kyle Petty
3-Dale Earnhardt
22-Ward Burton
45-Rich Bickle

Failed to qualify: Buckshot Jones, Dave Marcis, Hut Stricklin

After troubles by points leader Jeff Burton, Dale Jarrett would not only win this race, but inherit the points lead and hold it for the rest of 1999.
The Winston

, NASCAR's all-star race, was held May 22 at Lowe's Motor Speedway. Bobby Labonte won the pole.
Top ten results

5-Terry Labonte
20-Tony Stewart
24-Jeff Gordon
3-Dale Earnhardt
12-Jeremy Mayfield
60-Geoffrey Bodine
40-Sterling Marlin
7-Michael Waltrip
94-Bill Elliott
43-John Andretti

This was Terry Labonte's second win in the Winston. His first one came 11 years earlier in 1988, making this the longest time span between first and second wins in the All-Star Race for any driver in NASCAR history.
Coca-Cola 600

The Coca-Cola 600 was held May 30 at Lowe's Motor Speedway. Bobby Labonte won the pole.
Top ten results

99-Jeff Burton
18-Bobby Labonte
6-Mark Martin
20-Tony Stewart
88-Dale Jarrett
3-Dale Earnhardt
33-Ken Schrader
22-Ward Burton 1 lap down
31-Mike Skinner 1 lap down
12-Jeremy Mayfield 1 lap down

Dale Earnhardt Jr. made his NASCAR Winston Cup debut at this race, achieving a 16th-place finish.
Jeff Burton collected an extra million dollars for winning the third Winston No Bull 5 race of the season.

Failed to qualify: Jeff Green, Dick Trickle, Dave Marcis, Derrike Cope, Ricky Craven, Dan Pardus, Morgan Shepherd, Randy LaJoie, Carl Long

MBNA Platinum 400

The MBNA Platinum 400 was held June 6 at Dover Downs International Speedway. Bobby Labonte won the pole. For the second straight year in this race, fuel strategy did not play out in favor of Jeff Gordon, as he would again have to pit for fuel in the race's closing laps, giving the lead away to Bobby Labonte in this race who would lead the final six laps.
Top ten results

18-Bobby Labonte
24-Jeff Gordon
6-Mark Martin 1 lap down
20-Tony Stewart 1 lap down
88-Dale Jarrett 1 lap down
2-Rusty Wallace 1 lap down
26-Johnny Benson 1 lap down
99-Jeff Burton 1 lap down
12-Jeremy Mayfield 2 laps down
28-Kenny Irwin Jr. 2 laps down

Failed to qualify: Darrell Waltrip, Buckshot Jones, Hut Stricklin

Kmart 400

The Kmart 400 was held June 13 at Michigan Speedway. Jeff Gordon won the pole.
Top ten results

88-Dale Jarrett
24-Jeff Gordon
99-Jeff Burton
22-Ward Burton
18-Bobby Labonte
1-Steve Park 1 lap down
36-Ernie Irvan 1 lap down
43-John Andretti 1 lap down
20-Tony Stewart 2 laps down
6-Mark Martin 2 laps down

Failed to qualify: Dave Marcis, Hut Stricklin, Buckshot Jones

This race was run caution-free. It was therefore the fastest NASCAR Cup race at MIS, Dale Jarrett's average speed being 173.997 mph. As of 2020, this would be the last ever non-restrictor plate race to be caution-free. In 2017, NASCAR would make a three-stage format for every race of the season, and at a certain lap at the end of each stage, they would throw the caution flag, thus making it that a race can no longer be caution-free.
Pocono 500

The Pocono 500 was held June 20 at Pocono Raceway. Sterling Marlin won the pole. This race is mostly remembered for a hard crash from veteran Dave Marcis on Lap 91 when he got loose at turn two and when trying to correct it, spun hard right and slammed into the wall at a high rate of speed, getting some air and destroying his car. He emerged from the wreck without injury.
Top ten results

18-Bobby Labonte
24-Jeff Gordon
88-Dale Jarrett
40-Sterling Marlin
6-Mark Martin
20-Tony Stewart
3-Dale Earnhardt
36-Ernie Irvan
12-Jeremy Mayfield
4-Bobby Hamilton

Failed to qualify: Hut Stricklin, Loy Allen Jr., Derrike Cope

Save Mart/Kragen 350

The Save Mart/Kragen 350 was held June 27 at Sears Point Raceway. Jeff Gordon won the pole.
Top ten results

24-Jeff Gordon
6-Mark Martin
43-John Andretti
2-Rusty Wallace
23-Jimmy Spencer
88-Dale Jarrett
12-Jeremy Mayfield
44-Kyle Petty
3-Dale Earnhardt
7-Michael Waltrip

Failed to qualify: R. K. Smith, Austin Cameron, Sean Woodside, John Metcalf, Mike Borkowski, Boris Said, Steve Portenga, David Murry

Two flips occurred in the race, first when No. 1 of Steve Park got sideways in turn 1, hitting the guardrail and flipping once. He was uninjured. The No. 33 of Ken Schrader flipped as well in the same area of the track Park had crashed earlier. Schrader got sideways, causing the car to go over the fence and roll two and a half times. Schrader was also uninjured.
Jeff Gordon won the race despite hard charges by Mark Martin and being extremely sick. This was also Jeff's second straight win at Sears Point Raceway and his fourth straight win on a road course.
Pepsi 400

The Pepsi 400 was held July 3 at Daytona International Speedway. Joe Nemechek won the pole.
Top ten results

88-Dale Jarrett
3-Dale Earnhardt
99-Jeff Burton
31-Mike Skinner
18-Bobby Labonte
20-Tony Stewart
22-Ward Burton
4-Bobby Hamilton
36-Ernie Irvan
5-Terry Labonte

Failed to qualify: Derrike Cope, Hut Stricklin, Ken Bouchard, Robert Pressley, Stanton Barrett

This would be the 3rd and final time that "The Dale and Dale Show" finished 1st and 2nd at Daytona. Dale Jarrett defeated Dale Earnhardt in all 3 races.
With a couple of laps left, Jeremy Mayfield and Jimmy Spencer spun off of turn 4, bringing out the yellow flag and ending the race under the caution flag.
Final career top-10 for Ernie Irvan
Jiffy Lube 300

The Jiffy Lube 300 was held July 11 at New Hampshire International Speedway. Jeff Gordon won the pole.
Top ten results

99-Jeff Burton
55-Kenny Wallace
24-Jeff Gordon
88-Dale Jarrett
94-Bill Elliott
6-Mark Martin
25-Wally Dallenbach Jr.
3-Dale Earnhardt
23-Jimmy Spencer
20-Tony Stewart

Failed to qualify: Robert Pressley, Derrike Cope, David Green, Dave Marcis

Tony Stewart was only a couple of laps away from notching his first Winston Cup Series win when he ran out of fuel.
Pennsylvania 500

The Pennsylvania 500 was held July 25 at Pocono Raceway. Mike Skinner won the pole.
Top ten results

18-Bobby Labonte
88-Dale Jarrett
6-Mark Martin
20-Tony Stewart
25-Wally Dallenbach Jr.
5-Terry Labonte
45-Rich Bickle
1-Steve Park
3-Dale Earnhardt
31-Mike Skinner

Failed to qualify: Derrike Cope, Morgan Shepherd

With this win, Bobby Labonte completed a rare sweep of races at Pocono Raceway in one season.
Elliott Sadler injured his left foot during qualifying. Morgan Shepherd was on standby, but was not needed to relieve Elliott.
This was the final race where Ken Squier was the play-by-play announcer.
Brickyard 400

The Brickyard 400 was held August 7 at Indianapolis Motor Speedway. Jeff Gordon won the pole.
Top ten results

88-Dale Jarrett
18-Bobby Labonte
24-Jeff Gordon
6-Mark Martin
99-Jeff Burton
22-Ward Burton
20-Tony Stewart
2-Rusty Wallace
10-Ricky Rudd
3-Dale Earnhardt

Failed to qualify: Rich Bickle, Boris Said, Brett Bodine, Dick Trickle, Steve Grissom, Morgan Shepherd, Jeff Davis/Lance Hooper, Stanton Barrett, Mike Wallace, Gary Bradberry, Buckshot Jones, Bob Strait

Just one year after Jeff Gordon became the first repeat Brickyard 400 winner, Dale Jarrett redeemed himself after running out of fuel took him out of top contention in last year's race and followed in Gordon's footsteps to become the second repeat Brickyard 400 winner.
Frontier at the Glen

The Frontier at the Glen was held August 13 at Watkins Glen International. Rusty Wallace won the pole. Jeff Gordon would lead 55 of the race's 90 laps on his way to his third straight win at Watkins Glen and his fifth straight win overall on a road course.
Top ten results

24-Jeff Gordon
87-Ron Fellows*
2-Rusty Wallace
88-Dale Jarrett
9-Jerry Nadeau
20-Tony Stewart
25-Wally Dallenbach Jr.
44-Kyle Petty
31-Mike Skinner
6-Mark Martin

Failed to qualify: Robert Pressley, Derrike Cope, Paul Gentilozzi, Jack Baldwin, Hut Stricklin, Dave Marcis

5th consecutive road course win for Jeff Gordon.
This was Ernie Irvan's last NASCAR Winston Cup Race
Ron Fellows finished a career-best 2nd place finish in the #87 Bully Hill Vineyards Chevrolet.
Pepsi 400 Presented by Meijer

The Pepsi 400 Presented by Meijer was held August 22 at Michigan Speedway. Ward Burton won the pole.
Top ten results

18-Bobby Labonte
24-Jeff Gordon
20-Tony Stewart
88-Dale Jarrett
3-Dale Earnhardt
97-Chad Little
6-Mark Martin
23-Jimmy Spencer
58-Hut Stricklin
43-John Andretti

Failed to qualify: Derrike Cope, Stanton Barrett, Darrell Waltrip, Brett Bodine, Tom Hubert

This was the race that saw former Michigan winner Ernie Irvan crashed hard during Busch Series practice, similar to a crash that he was involved in during the 1994 event. Dick Trickle subbed for Irvan for this race and then Jerry Nadeau took over for the remainder of the season.
Goody's Headache Powder 500

The Goody's Headache Powder 500 was held August 28 at Bristol Motor Speedway. Tony Stewart won the pole.
Top ten results

3-Dale Earnhardt
23-Jimmy Spencer
10-Ricky Rudd
24-Jeff Gordon
20-Tony Stewart
6-Mark Martin
40-Sterling Marlin
5-Terry Labonte
22-Ward Burton
33-Ken Schrader

This race came under some controversy when on the last lap, Dale Earnhardt spun out leader Terry Labonte, who collected Ricky Rudd and Stewart. Earnhardt was booed as he pulled into victory lane. On lap 490, Earnhardt would inherit the lead after leader Terry Labonte spun after the caution flag was just brought out with 9 laps to go. Because of the low number of lead lap cars left in the race, Terry was able to pit for tires during the caution flag and make a hard charge to the front when the race was back green. Labonte got by Earnhardt for the lead coming to the white flag then Earnhardt got into him in turns 1 and 2.

Failed to qualify: Rich Bickle, Dick Trickle

Pepsi Southern 500

The 50th Pepsi Southern 500 was held September 5 at Darlington Raceway. Kenny Irwin Jr. won the pole.
Top ten results

99-Jeff Burton
22-Ward Burton
12-Jeremy Mayfield
6-Mark Martin
16-Kevin Lepage
42-Joe Nemechek
4-Bobby Hamilton
2-Rusty Wallace
33-Ken Schrader
1-Steve Park

Failed to qualify: Todd Bodine, Stanton Barrett

Jeff Burton once again collected one million dollars for his victory in the fourth Winston No Bull 5 race of 1999.
The race was halted on lap 270 due to rain.
During the weekend of this race, Ernie Irvan announced his immediate retirement from racing due to injuries he suffered while testing his Busch Series car at Michigan International Speedway the previous month.
Exide NASCAR Select Batteries 400

The Exide NASCAR Select Batteries 400 was held September 11 at Richmond International Raceway. Mike Skinner won the pole.
Top ten results

20-Tony Stewart*
18-Bobby Labonte
88-Dale Jarrett
40-Sterling Marlin
28-Kenny Irwin Jr.
3-Dale Earnhardt
4-Bobby Hamilton
75-Ted Musgrave
43-John Andretti 1 lap down
8-Dale Earnhardt Jr. 1 lap down

Failed to qualify: Jack Sprague, Dave Marcis, Hut Stricklin, Stanton Barrett, Tommy Baldwin Sr.

This was Tony Stewart's first NASCAR Winston Cup win. Stewart led 333 of the race's 400 laps.
Stewart would be the first rookie since Davey Allison in 1987 to win a NASCAR points race.
First career top ten for Dale Earnhardt Jr.
Last career top ten for Ted Musgrave.
Dura Lube/Kmart 300

The Dura Lube/Kmart 300 was held September 19 at New Hampshire International Speedway. Rusty Wallace won the pole.
Top ten results

42-Joe Nemechek*
20-Tony Stewart
18-Bobby Labonte
99-Jeff Burton
24-Jeff Gordon
2-Rusty Wallace
26-Johnny Benson
22-Ward Burton
98-Rick Mast
28-Kenny Irwin Jr.

Failed to qualify: Darrell Waltrip, Derrike Cope, Dick Trickle, Andy Belmont

This was Joe Nemechek's first NASCAR Winston Cup win.
For the second week in a row, a first-time winner won the race.
This race ended under the caution flag.
MBNA Gold 400

The MBNA Gold 400 was held September 26 at Dover Downs International Speedway. Rusty Wallace won the pole.
Top ten results

6-Mark Martin
20-Tony Stewart
88-Dale Jarrett
17-Matt Kenseth
18-Bobby Labonte
99-Jeff Burton
97-Chad Little 1 lap down
3-Dale Earnhardt 1 lap down
1-Steve Park 1 lap down
28-Kenny Irwin Jr. 1 lap down

Failed to qualify: Dick Trickle, Todd Bodine, Darrell Waltrip, Derrike Cope, Andy Belmont

First career top-5 for Matt Kenseth.
NAPA AutoCare 500

The NAPA AutoCare 500 was held October 3 at Martinsville Speedway. Joe Nemechek won the pole.
Top ten results

24-Jeff Gordon
3-Dale Earnhardt
60-Geoffrey Bodine
2-Rusty Wallace
55-Kenny Wallace
31-Mike Skinner
44-Kyle Petty
18-Bobby Labonte
99-Jeff Burton 1 lap down
88-Dale Jarrett 1 lap down

Failed to qualify: Ron Hornaday Jr., Dick Trickle, Tim Fedewa, Morgan Shepherd

It was announced prior to this race, that Jeff Gordon's crew chief Ray Evernham was leaving Hendrick Motorsports to oversee Dodge's return to NASCAR in 2001. Brian Whitesell was Gordon's crew chief for the remainder of 1999.
UAW-GM Quality 500

The UAW-GM Quality 500 at Lowe's Motor Speedway was scheduled for October 10 but was held October 11 due to rain. Bobby Labonte won the pole.
Top ten results

24-Jeff Gordon
18-Bobby Labonte
31-Mike Skinner
6-Mark Martin
22-Ward Burton
12-Jeremy Mayfield
88-Dale Jarrett
2-Rusty Wallace 1 lap down
16-Kevin Lepage 1 lap down
1-Steve Park 1 lap down

Failed to qualify: Darrell Waltrip, Dave Marcis, Ed Berrier, Gary Bradberry, Hut Stricklin, Andy Hillenburg

With this win, Jeff Gordon was now two for two with Brian Whitesell as his interim crew chief, as the tandem had won their first race together a week ago at Martinsville.
1999 marked the 5th consecutive year that Jeff Gordon won 7+ races in a season, a NASCAR modern era record. In 1995, he won 7 races, in both 1996 and 1997, he won 10 races in each season, and in 1998, he won 13 races. 1999 also marked the 5th consecutive year for Jeff Gordon winning the most races in a season, another NASCAR modern era record. As of 2019, Gordon is so far still the only driver in NASCAR history to accomplish this feat.
This was the 49th career win for Jeff Gordon. This win would tie him with Rusty Wallace for 10th on the NASCAR all time win list.
Final win of 1999 for Jeff Gordon.
Winston 500

The Winston 500 was held October 17 at Talladega Superspeedway. Joe Nemechek won the pole.
Top ten results

3-Dale Earnhardt
88-Dale Jarrett
10-Ricky Rudd
22-Ward Burton
55-Kenny Wallace
20-Tony Stewart
18-Bobby Labonte
99-Jeff Burton
4-Bobby Hamilton
28-Kenny Irwin Jr.

Failed to qualify: Bobby Gerhart, Robert Pressley, Darrell Waltrip, Hut Stricklin

As of 2020, Dale Earnhardt is the only driver in NASCAR history to pull off the season sweep at Talladega twice. His other season sweep was back in 1990. Drivers that pulled off the season sweep before him only did it once. Those drivers are Pete Hamilton back in 1970, Buddy Baker in 1975, and Darrell Waltrip in 1982. His son Dale Earnhardt Jr. would pull off the season sweep in 2002, and Jeff Gordon would do so as well in 2007.
This was the final Winston No Bull 5 race of 1999. The top five finishing order would be eligible for the bonus at the 2000 Daytona 500.
Pop Secret Microwave Popcorn 400

The Pop Secret Microwave Popcorn 400 was held October 24 at North Carolina Speedway. Mark Martin won the pole.
Top ten results

99-Jeff Burton
22-Ward Burton
18-Bobby Labonte
88-Dale Jarrett
2-Rusty Wallace
6-Mark Martin
43-John Andretti
40-Sterling Marlin
12-Jeremy Mayfield 1 lap down
4-Bobby Hamilton 1 lap down

Failed to qualify: Dave Marcis, Rich Bickle, Hut Stricklin, Ed Berrier

This would be the third time this season that the Burton brothers would finish 1-2, with younger brother Jeff winning all three races over older brother Ward. Three times would be the most times in one season that a set of brothers finished first and second.
During the weekend for this race, the No. 58 SBIII Motorsports team closed its doors due to a sponsorship pullout.
Checker Auto Parts/Dura Lube 500

The Checker Auto Parts/Dura Lube 500 was held November 7 at Phoenix International Raceway. John Andretti won the pole.
Top ten results

20-Tony Stewart
6-Mark Martin
18-Bobby Labonte
99-Jeff Burton
10-Ricky Rudd
88-Dale Jarrett
44-Kyle Petty
43-John Andretti
25-Wally Dallenbach Jr.
24-Jeff Gordon

Failed to qualify: Mike Wallace

Tony Stewart would be the first rookie since Davey Allison in 1987 to win two races in his rookie season.
Pennzoil 400 Presented by Kmart

The inaugural Pennzoil 400 Presented by Kmart was held November 14 at Homestead-Miami Speedway. David Green won the pole. This was the first NASCAR Cup Series race televised on NBC Sports.
Top ten results

20-Tony Stewart
18-Bobby Labonte
99-Jeff Burton
6-Mark Martin
88-Dale Jarrett
31-Mike Skinner
44-Kyle Petty
3-Dale Earnhardt 1 lap down
25-Wally Dallenbach Jr. 1 lap down
24-Jeff Gordon 1 lap down

Failed to qualify: Dave Marcis, Ed Berrier, Derrike Cope, Andy Belmont, Bob Strait

This was Ted Musgrave's final race as a full-time Winston Cup series regular. Musgrave quit the Butch Mock Motorsports team after this race. He would later re-surface in the Craftsman Truck Series and find success, winning 15 career races and the series championship in 2005.
Dale Jarrett clinched the Winston Cup Series championship with one race to go. In Bob Latford's Winston Cup points system, a driver can clinch the championship with one race to go if he has a point margin of 185+ over 2nd, and Jarrett did just that by having a 211 point lead over Bobby Labonte at the end of the race.
Tony Stewart won his 3rd race of 1999, breaking Davey Allison's record for most wins in a rookie season. He would become the 1st rookie to win 3 races in one season. Stewart also became the 1st, and as of 2020, the only rookie in NASCAR history to win back-to-back races.
NAPA 500

The NAPA 500 was held November 21 at Atlanta Motor Speedway. Kevin Lepage won the pole.
Top ten results

18-Bobby Labonte
88-Dale Jarrett
12-Jeremy Mayfield
6-Mark Martin
99-Jeff Burton
97-Chad Little
10-Ricky Rudd
31-Mike Skinner
3-Dale Earnhardt
4-Bobby Hamilton

Failed to qualify: Darrell Waltrip, Derrike Cope, Hut Stricklin, Ricky Craven, Stacy Compton, Morgan Shepherd

Bobby Labonte won the 1999 NAPA 500, despite taking a provisional to make the race. He started back in the 37th position.
Dale Jarrett would officially finish his championship season 201 points over runner-up Bobby Labonte.
Dale Jarrett's 1999 Championship season came with 29 top 10 finishes in 34 races, which was a NASCAR record. That record stood until the 2007 season when Jeff Gordon finished with 30 top 10s in 36 races.
Final points standings

Bold - Pole position awarded by time. Italics - Pole position set by owner's points standings.

Pos	Driver	DAY	CAR	LVS	ATL	DAR	TEX	BRI	MAR	TAL	CAL	RCH	CLT	DOV	MCH	POC	SON	DAY	NHA	POC	IND	GLN	MCH	BRI	DAR	RCH	NHA	DOV	MAR	CLT	TAL	CAR	PHO	HOM	ATL	Points
1	Dale Jarrett	37	2	11	5	4	2	3	8	2	5	1	5	5	1	3	6	1	4	2	1	4	4	38	16	3	18	3	10	7	2	4	6	5	2	5262
2	Bobby Labonte	25	3	5	2	10	3	37	24	4	3	3	2	1	5	1	27	5	38	1	2	24	1	26	19	2	3	5	8	2	7	3	3	2	1	5061
3	Mark Martin	31	1	10	3	5	34	2	5	3	38	2	3	3	10	5	2	17	6	3	4	10	7	6	4	35	17	1	16	4	15	6	2	4	4	4943
4	Tony Stewart	28	12	36	11	6	6	15	20	5	4	15	4	4	9	6	15	6	10	4	7	6	3	5	12	1	2	2	41	19	6	12	1	1	15	4774
5	Jeff Burton	35	4	1	4	1	7	5	2	11	2	37	1	8	3	36	24	3	1	36	5	13	37	17	1	13	4	6	9	37	8	1	4	3	5	4733
6	Jeff Gordon	1	39	3	1	3	43	6	3	38	1	31	39	2	2	2	1	21	3	32	3	1	2	4	13	40	5	17	1	1	12	11	10	10	38	4620
7	Dale Earnhardt	2	41	7	40	25	8	10	19	1	12	8	6	11	16	7	9	2	8	9	10	20	5	1	22	6	13	8	2	12	1	40	11	8	9	4492
8	Rusty Wallace	8	10	9	35	33	4	1	7	41	11	5	31	6	12	43	4	11	42	18	8	3	16	18	8	14	6	32	4	8	11	5	32	12	13	4155
9	Ward Burton	24	28	2	8	8	16	9	27	32	6	9	8	22	4	29	35	7	15	40	6	43	43	9	2	34	8	11	13	5	4	2	13	14	11	4062
10	Mike Skinner	4	6	4	6	32	42	21	4	36	10	30	9	19	18	22	17	4	23	10	12	9	36	23	36	11	27	21	6	3	13	17	20	6	8	4003
11	Jeremy Mayfield	20	5	17	36	2	5	27	41	15	7	24	10	9	17	9	7	25	28	35	29	34	18	32	3	25	36	22	15	6	16	9	41	13	3	3743

88-Dale Jarrett - 5262
18-Bobby Labonte - 5061
6-Mark Martin - 4943
20-Tony Stewart ' - 4774
99-Jeff Burton - 4733
24-Jeff Gordon - 4620
3-Dale Earnhardt - 4492
2-Rusty Wallace - 4155
22-Ward Burton - 4062
31-Mike Skinner - 4003
12-Jeremy Mayfield - 3743
5-Terry Labonte - 3580
4-Bobby Hamilton - 3564
1-Steve Park - 3481
33-Ken Schrader - 3479
40-Sterling Marlin - 3397
43-John Andretti - 3394
25-Wally Dallenbach Jr. - 3367
28-Kenny Irwin Jr. - 3338
23-Jimmy Spencer - 3307
94-Bill Elliott - 3246
55-Kenny Wallace - 3210
97-Chad Little - 3193
21-Elliott Sadler ' - 3191
16-Kevin Lepage - 3185
44-Kyle Petty - 3103
60-Geoffrey Bodine - 3053
26-Johnny Benson - 3012
7-Michael Waltrip - 2974
42-Joe Nemechek - 2956
10-Ricky Rudd - 2922
98-Rick Mast - 2845
75-Ted Musgrave - 2689
9/36-Jerry Nadeau - 2686
11-Brett Bodine - 2351
41/45-David Green - 2320
66-Darrell Waltrip - 2158
45/9-Rich Bickle - 2149
77-Robert Pressley - 2050
36-Ernie Irvan - 1915
58/50-Ricky Craven - 1513
71-Dave Marcis - 1324
90/58-Hut Stricklin - 918
30/41-Derrike Cope - 915
00-Buckshot Jones ' - 676
30-Todd Bodine - 529
91-Dick Trickle - 528
8-Dale Earnhardt Jr. - 500
17-Matt Kenseth - 434
91/9-Steve Grissom - 336
93-Dave Blaney - 332
90-Ed Berrier - 268
32-Mike Wallace - 185
87-Ron Fellows - 175
9-Stacy Compton - 174
19-Tom Hubert - 143
90-Stanton Barrett ' - 143
30-Mike Bliss - 104
14-Boris Said - 103
01-Jeff Green - 100
14-Randy LaJoie - 95
58-Loy Allen Jr. - 86
01-Ron Hornaday Jr. - 76
13-Ted Christopher - 70
90-Morgan Shepherd - 67
41-Gary Bradberry - 58
61-David Murry - 46
91-Andy Hillenburg - 34
38-Butch Gilliland - 34
Rookie of the Year

The 1999 Rookie of the Year battle was expected to be one of the most competitive in years. In the end, it was a runaway as Tony Stewart won three races and finished fourth in points. Elliott Sadler, who was considered the top favorite for the award during the pre-season, only had one top-ten finish and was the only rookie besides Stewart to complete the full schedule. Buckshot Jones was another favorite, but a long string of DNQs and DNFs forced him to cut back his schedule and abandon his run for the award. Stanton Barrett began the year with his own team, then left for Junie Donlavey, only making two races. Dan Pardus hoped to run a part-time schedule with Midwest Transit Racing, but he did not qualify for any of his attempts, and was released after the Coca-Cola 600. Finally, Mike Harmon was scheduled to drive the No. 90, but did not even attempt a race after a sponsorship fallout with Big Daddy's BBQ Sauce.

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1999 NASCAR Winston Cup Series

Teams and drivers

Complete schedule

Limited schedule

Schedule

Races

Daytona 500

California 500 Presented by NAPA

The Winston

Final points standings

Gallery