1999 NASCAR Winston Cup Series

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

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

1. 6-Mark Martin
2. 33-Ken Schrader
3. 18-Bobby Labonte
4. 31-Mike Skinner
5. 12-Jeremy Mayfield
6. 22-Ward Burton
7. 2-Rusty Wallace
8. 88-Dale Jarrett
9. 98-Rick Mast
10. 28-Kenny Irwin Jr.

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

1. 18-Bobby Labonte
2. 24-Jeff Gordon
3. 99-Jeff Burton
4. 33-Ken Schrader
5. 6-Mark Martin
6. 26-Jimmy Spencer
7. 7-Michael Waltrip
8. 77-Robert Pressley
9. 40-Sterling Marlin
10. 5-Terry Labonte

Race two: top ten results

1. 3-Dale Earnhardt
2. 12-Jeremy Mayfield
3. 88-Dale Jarrett
4. 2-Rusty Wallace
5. 31-Mike Skinner
6. 20-Tony Stewart
7. 16-Kevin Lepage
8. 4-Bobby Hamilton
9. 22-Ward Burton
10. 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 (1990-1999), becoming the only driver in NASCAR history to win an event for an entire decade. This would also be Dale Earnhardt's 28th and final career Daytona NASCAR win. Along with his 12 Gatorade 125 wins, he has 7 wins in the season opener for the Busch Series, 6 wins in the Busch Clash, 2 wins in the Pepsi 400, and a win in the 1998 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.

1. 24-Jeff Gordon
2. 3-Dale Earnhardt
3. 28-Kenny Irwin Jr.
4. 31-Mike Skinner
5. 7-Michael Waltrip
6. 33-Ken Schrader
7. 44-Kyle Petty
8. 2-Rusty Wallace
9. 97-Chad Little
10. 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, 79-Norm Benning.

• This would be the 3rd and final time in his career that Jeff Gordon would win 3 straight NASCAR races (last 2 races of 1998 and 1st race of 1999).
• 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.

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

Top ten results

1. 6-Mark Martin
2. 88-Dale Jarrett
3. 18-Bobby Labonte
4. 99-Jeff Burton
5. 12-Jeremy Mayfield
6. 31-Mike Skinner
7. 5-Terry Labonte
8. 60-Geoff Bodine
9. 4-Bobby Hamilton
10. 2-Rusty Wallace

Failed to qualify: Derrike Cope (No. 30), Buckshot Jones (No. 00), Billy Standridge (No. 50), Rich Bickle (No. 45)

• Jeff Gordon lost his bid at another 4 straight victories (which would be the last 2 races of 1998 and the 1st race of 1999, the Daytona 500), 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.

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

1. 99-Jeff Burton
2. 22-Ward Burton
3. 24-Jeff Gordon
4. 31-Mike Skinner
5. 18-Bobby Labonte
6. 36-Ernie Irvan
7. 3-Dale Earnhardt
8. 5-Terry Labonte
9. 2-Rusty Wallace
10. 6-Mark Martin

Failed to qualify: Ted Musgrave (No. 75), Kyle Petty (No. 44), Robert Pressley (No. 77), Ron Hornaday Jr. (No. 50), Butch Gilliland (No. 38), Dave Marcis (No. 71), Morgan Shepherd (No. 92), Ron Burns (No. 68), Austin Cameron (No. 89)

• This was the second Winston No Bull 5 race for 1999.

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

Top ten results

1. 24-Jeff Gordon
2. 18-Bobby Labonte
3. 6-Mark Martin
4. 99-Jeff Burton
5. 88-Dale Jarrett
6. 31-Mike Skinner
7. 36-Ernie Irvan
8. 22-Ward Burton
9. 97-Chad Little
10. 7-Michael Waltrip

Failed to qualify: Robert Pressley (No. 77), Steve Grissom (No. 91), Morgan Shepherd (No. 90), Harris DeVane (No. 08)

• This would be Jeff Gordon's 35th win in 100 straight races, and in the last 100 NASCAR Cup Series Races as well (both all-time records). His streak began when he won at Richmond, the 3rd race of the 1996 season.

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 (the leader at the time) 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

1. 99-Jeff Burton
2. 12-Jeremy Mayfield
3. 24-Jeff Gordon
4. 88-Dale Jarrett
5. 6-Mark Martin
6. 20-Tony Stewart
7. 4-Bobby Hamilton
8. 22-Ward Burton
9. 43-John Andretti
10. 18-Bobby Labonte

Failed to qualify: Derrike Cope (No. 30), Dave Marcis (No. 71), Rich Bickle (No. 45)

• First career top-10 for Tony Stewart.

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

Top ten results

1. 5-Terry Labonte
2. 88-Dale Jarrett
3. 18-Bobby Labonte
4. 2-Rusty Wallace
5. 12-Jeremy Mayfield
6. 20-Tony Stewart
7. 99-Jeff Burton
8. 3-Dale Earnhardt
9. 40-Sterling Marlin
10. 21-Elliott Sadler

Failed to qualify: Dick Trickle (No. 91), Stanton Barrett (No. 90), Kyle Petty (No. 44), Dave Marcis (No. 71), Ken Bouchard (No. 84)

• 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 of only three times in his career that Jeff Gordon finished last in a 43-car field. Coincidentally, the only other time he finished 43rd out of 43 cars was at Texas again in 2008.

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

Top ten results

1. 2-Rusty Wallace
2. 6-Mark Martin
3. 88-Dale Jarrett
4. 43-John Andretti
5. 99-Jeff Burton
6. 24-Jeff Gordon
7. 75-Ted Musgrave
8. 44-Kyle Petty
9. 22-Ward Burton
10. 3-Dale Earnhardt

Failed to qualify: Rich Bickle (No. 45), Stanton Barrett (No. 90), Derrike Cope (No. 30), Carl Long (No. 85)

• 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.

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

Top ten results

1. 43-John Andretti
2. 99-Jeff Burton
3. 24-Jeff Gordon
4. 31-Mike Skinner
5. 6-Mark Martin
6. 55-Kenny Wallace
7. 2-Rusty Wallace
8. 88-Dale Jarrett
9. 33-Ken Schrader
10. 44-Kyle Petty

Failed to qualify: Dave Marcis (No. 71), Morgan Shepherd (No. 90), Buckshot Jones (No. 00)

• 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.

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

Top ten results

1. 3 -Dale Earnhardt
2. 88-Dale Jarrett
3. 6 -Mark Martin
4. 18-Bobby Labonte
5. 20-Tony Stewart
6. 33-Ken Schrader
7. 55-Kenny Wallace
8. 9 -Jerry Nadeau
9. 43-John Andretti
10. 94-Bill Elliott

Failed to qualify: Ken Bouchard (No. 84), Dan Pardus (No. 50), Derrike Cope (No. 30), Loy Allen Jr. (No. 90), Dick Trickle (No. 91)

• First career top-5 for Tony Stewart.

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

1. 24-Jeff Gordon
2. 99-Jeff Burton
3. 18-Bobby Labonte
4. 20-Tony Stewart
5. 88-Dale Jarrett
6. 22-Ward Burton
7. 12-Jeremy Mayfield
8. 25-Wally Dallenbach Jr.
9. 5-Terry Labonte
10. 31-Mike Skinner 1 lap down

Failed to qualify: Boris Said (No. 14), Hut Stricklin (No. 90), Buckshot Jones (No. 00), Butch Gilliland (No. 38)

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

Top ten results

1. 88-Dale Jarrett
2. 6-Mark Martin
3. 18-Bobby Labonte
4. 4-Bobby Hamilton
5. 2-Rusty Wallace
6. 42-Joe Nemechek
7. 44-Kyle Petty
8. 3-Dale Earnhardt
9. 22-Ward Burton
10. 45-Rich Bickle

Failed to qualify: Buckshot Jones (No. 00), Dave Marcis (No. 71), Hut Stricklin (No. 90)

• 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

1. 5-Terry Labonte
2. 20-Tony Stewart
3. 24-Jeff Gordon
4. 3-Dale Earnhardt
5. 12-Jeremy Mayfield
6. 60-Geoff Bodine
7. 40-Sterling Marlin
8. 7-Michael Waltrip
9. 94-Bill Elliott
10. 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.

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

Top ten results

1. 99-Jeff Burton
2. 18-Bobby Labonte
3. 6-Mark Martin
4. 20-Tony Stewart
5. 88-Dale Jarrett
6. 3-Dale Earnhardt
7. 33-Ken Schrader
8. 22-Ward Burton 1 lap down
9. 31-Mike Skinner 1 lap down
10. 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 (No. 01), Dick Trickle (No. 91), Dave Marcis (No. 71), Derrike Cope (No. 30), Ricky Craven (No. 58), Dan Pardus (No. 50), Morgan Shepherd (No. 05), Randy LaJoie (No. 14), Carl Long (No. 85)

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

1. 18-Bobby Labonte
2. 24-Jeff Gordon
3. 6-Mark Martin 1 lap down
4. 20-Tony Stewart 1 lap down
5. 88-Dale Jarrett 1 lap down
6. 2-Rusty Wallace 1 lap down
7. 26-Johnny Benson 1 lap down
8. 99-Jeff Burton 1 lap down
9. 12-Jeremy Mayfield 2 laps down
10. 28-Kenny Irwin Jr. 2 laps down

Failed to qualify: Darrell Waltrip (No. 66), Buckshot Jones (No. 00), Hut Stricklin (No. 90)

• This was Darrell Waltrip's first DNQ since the 1997 UAW-GM Quality 500 at Charlotte. As NASCAR has implemented a maximum limit of the past champion's provisional to a total of eight, Waltrip had exhausted all of his provisionals prior to this race. He would miss a total of seven races this season.[2]
• As of 2021, this is the last time where only two drivers finish on the lead lap.

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

Top ten results

1. 88-Dale Jarrett
2. 24-Jeff Gordon
3. 99-Jeff Burton
4. 22-Ward Burton
5. 18-Bobby Labonte
6. 1-Steve Park 1 lap down
7. 36-Ernie Irvan 1 lap down
8. 43-John Andretti 1 lap down
9. 20-Tony Stewart 2 laps down, DNF-out of gas.
10. 6-Mark Martin 2 laps down

Failed to qualify: Dave Marcis (No. 71), Hut Stricklin (No. 90), Buckshot Jones (No. 00)

• This race was run caution-free. It was therefore the fastest NASCAR Cup race at MIS, with Dale Jarrett's average speed being 173.997 mph. As of 2021, 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.
• This was the last career Winston Cup race in which Ernie Irvan lead a lap.

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 speed, getting some air and destroying his car. He emerged from the wreck without injury.

Top ten results

1. 18-Bobby Labonte
2. 24-Jeff Gordon
3. 88-Dale Jarrett
4. 40-Sterling Marlin
5. 6-Mark Martin
6. 20-Tony Stewart
7. 3-Dale Earnhardt
8. 36-Ernie Irvan
9. 12-Jeremy Mayfield
10. 4-Bobby Hamilton

Failed to qualify: Hut Stricklin (No. 90), Loy Allen Jr. (No. 58), Derrike Cope (No. 30)

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

Top ten results

1. 24-Jeff Gordon
2. 6-Mark Martin
3. 43-John Andretti
4. 2-Rusty Wallace
5. 23-Jimmy Spencer
6. 88-Dale Jarrett
7. 12-Jeremy Mayfield
8. 44-Kyle Petty
9. 3-Dale Earnhardt
10. 7-Michael Waltrip

Failed to qualify: R. K. Smith (No. 71), Austin Cameron (No. 89), Sean Woodside (No. 58), John Metcalf (No. 70), Mike Borkowski (No. 09), Boris Said (No. 14), Steve Portenga (No. 96), David Murry (No. 61)

• Two flips occurred in the race: First when the 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.
• Former Formula 1 driver Érik Comas was going to attempt his Cup Series debut for Donlavey Racing, but the deal fell through and Donlavey did not attempt this race.

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

Top ten results

1. 88-Dale Jarrett
2. 3-Dale Earnhardt
3. 99-Jeff Burton
4. 31-Mike Skinner
5. 18-Bobby Labonte
6. 20-Tony Stewart
7. 22-Ward Burton
8. 4-Bobby Hamilton
9. 36-Ernie Irvan
10. 5-Terry Labonte

Failed to qualify: Derrike Cope (No. 30), Hut Stricklin (No. 91), Ken Bouchard (No. 84), Robert Pressley (No. 77), Stanton Barrett (No. 90)

• 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 (1993 & 1996 Daytona 500s, and 1999 Pepsi 400).
• 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.

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

Top ten results

1. 99-Jeff Burton
2. 55-Kenny Wallace
3. 24-Jeff Gordon
4. 88-Dale Jarrett
5. 94-Bill Elliott
6. 6-Mark Martin
7. 25-Wally Dallenbach Jr.
8. 3-Dale Earnhardt
9. 23-Jimmy Spencer
10. 20-Tony Stewart

Failed to qualify: Robert Pressley (No. 77), Derrike Cope (No. 30), David Green (No. 41), Dave Marcis (No. 71)

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

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

Top ten results

1. 18-Bobby Labonte
2. 88-Dale Jarrett
3. 6-Mark Martin
4. 20-Tony Stewart
5. 25-Wally Dallenbach Jr.
6. 5-Terry Labonte
7. 45-Rich Bickle
8. 1-Steve Park
9. 3-Dale Earnhardt
10. 31-Mike Skinner

Failed to qualify: Derrike Cope (No. 30), Morgan Shepherd (No. 91)

• 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.

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

Top ten results

1. 88-Dale Jarrett
2. 18-Bobby Labonte
3. 24-Jeff Gordon
4. 6-Mark Martin
5. 99-Jeff Burton
6. 22-Ward Burton
7. 20-Tony Stewart
8. 2-Rusty Wallace
9. 10-Ricky Rudd
10. 3-Dale Earnhardt

Failed to qualify: Rich Bickle (No. 45), Boris Said (No. 14), Brett Bodine (No. 11), Dick Trickle (No. 91), Steve Grissom (No. 01), Morgan Shepherd (No. 05), Jeff Davis/Lance Hooper (No. 62), Stanton Barrett (No. 90), Mike Wallace (No. 32), Gary Bradberry (No. 80), Buckshot Jones (No. 00), Bob Strait (No. 61)

• 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.
• Jarrett's victory would be the last time a Ford would take the checkered flag first at this race until Brad Keselowski's victory in 2018, nearly 20 years later.

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

1. 24-Jeff Gordon
2. 87-Ron Fellows*
3. 2-Rusty Wallace
4. 88-Dale Jarrett
5. 9-Jerry Nadeau
6. 20-Tony Stewart
7. 25-Wally Dallenbach Jr.
8. 44-Kyle Petty
9. 31-Mike Skinner
10. 6-Mark Martin

Failed to qualify: Robert Pressley (No. 77), Derrike Cope (No. 30), Paul Gentilozzi (No. 19), Jack Baldwin (No. 91), Hut Stricklin (No. 58), Dave Marcis (No. 71)

• 5th consecutive road course win for Jeff Gordon.
• This would unexpectedly be the 47th and final career victory for Ray Evernham as a crew chief.
• 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.
• This was Jack Baldwin's lone Cup Series qualifying attempt

The Pepsi 400 presented by Meijer was held August 22 at Michigan Speedway. Ward Burton won the pole.

Top ten results

1. 18-Bobby Labonte
2. 24-Jeff Gordon
3. 20-Tony Stewart
4. 88-Dale Jarrett
5. 3-Dale Earnhardt
6. 97-Chad Little
7. 6-Mark Martin
8. 23-Jimmy Spencer
9. 58-Hut Stricklin
10. 43-John Andretti

Failed to qualify: Derrike Cope (No. 30), Stanton Barrett (No. 90), Darrell Waltrip (No. 66), Brett Bodine (No. 11), Tom Hubert (No. 19)

• This was the race weekend that saw former Michigan winner Ernie Irvan crash 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.
• Also during the race weekend Team SABCO and Joe Nemechek announced that they would part ways at the end of the season.[3]

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

Top ten results

1. 3-Dale Earnhardt
2. 23-Jimmy Spencer
3. 10-Ricky Rudd
4. 24-Jeff Gordon
5. 20-Tony Stewart
6. 6-Mark Martin
7. 40-Sterling Marlin
8. 5-Terry Labonte 1 lap down
9. 22-Ward Burton 1 lap down
10. 33-Ken Schrader 1 lap down

• 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 (No. 45), Dick Trickle (No. 91)

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

Top ten results

1. 99-Jeff Burton
2. 22-Ward Burton
3. 12-Jeremy Mayfield
4. 6-Mark Martin
5. 16-Kevin Lepage
6. 42-Joe Nemechek
7. 4-Bobby Hamilton
8. 2-Rusty Wallace
9. 33-Ken Schrader
10. 1-Steve Park

Failed to qualify: Todd Bodine (No. 30), Stanton Barrett (No. 90)

• 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.

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

Top ten results

1. 20-Tony Stewart*
2. 18-Bobby Labonte
3. 88-Dale Jarrett
4. 40-Sterling Marlin
5. 28-Kenny Irwin Jr.
6. 3-Dale Earnhardt
7. 4-Bobby Hamilton
8. 75-Ted Musgrave
9. 43-John Andretti 1 lap down
10. 8-Dale Earnhardt Jr. 1 lap down

Failed to qualify: Jack Sprague (No. 45), Dave Marcis (No. 71), Hut Stricklin (No. 58), Stanton Barrett (No. 90), Tom Baldwin (No. 91)

• 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.

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

Top ten results

1. 42-Joe Nemechek*
2. 20-Tony Stewart
3. 18-Bobby Labonte
4. 99-Jeff Burton
5. 24-Jeff Gordon
6. 2-Rusty Wallace
7. 26-Johnny Benson
8. 22-Ward Burton
9. 98-Rick Mast
10. 28-Kenny Irwin Jr.

Failed to qualify: Darrell Waltrip (No. 66), Derrike Cope (No. 91), Dick Trickle (No. 41), Andy Belmont (No. 79)

• This was Joe Nemechek's first NASCAR Winston Cup win. It was bittersweet as weeks earlier it was announced that Joe would not return to Team SABCO for the year 2000.
• For the second week in a row, a first-time winner won the race.
• This race ended under the caution flag.

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

Top ten results

1. 6-Mark Martin
2. 20-Tony Stewart
3. 88-Dale Jarrett
4. 17-Matt Kenseth
5. 18-Bobby Labonte
6. 99-Jeff Burton
7. 97-Chad Little 1 lap down
8. 3-Dale Earnhardt 1 lap down
9. 1-Steve Park 1 lap down
10. 28-Kenny Irwin Jr. 1 lap down

Failed to qualify: Dick Trickle (No. 41), Todd Bodine (No. 30), Darrell Waltrip (No. 66), Derrike Cope (No. 91), Andy Belmont (No. 79)

• First career top-5 for Matt Kenseth.
• First time in his career that Darrell Waltrip would fail to qualify back-to-back races.

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

Top ten results

1. 24-Jeff Gordon
2. 3-Dale Earnhardt
3. 60-Geoff Bodine
4. 2-Rusty Wallace
5. 55-Kenny Wallace
6. 31-Mike Skinner
7. 44-Kyle Petty
8. 18-Bobby Labonte
9. 99-Jeff Burton 1 lap down
10. 88-Dale Jarrett 1 lap down

Failed to qualify: Ron Hornaday Jr. (No. 01), Dick Trickle (No. 41), Tim Fedewa (No. 91), Morgan Shepherd (No. 05)

• 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.

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

1. 24-Jeff Gordon
2. 18-Bobby Labonte
3. 31-Mike Skinner
4. 6-Mark Martin
5. 22-Ward Burton
6. 12-Jeremy Mayfield
7. 88-Dale Jarrett
8. 2-Rusty Wallace 1 lap down
9. 16-Kevin Lepage 1 lap down
10. 1-Steve Park 1 lap down

Failed to qualify: Darrell Waltrip (No. 66), Dave Marcis (No. 71), Ed Berrier (No. 90), Gary Bradberry (No. 80), Hut Stricklin (No. 58), Andy Hillenburg (No. 91)

• 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 2020, 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.
• 7th and final win of 1999 for Jeff Gordon.

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

Top ten results

1. 3-Dale Earnhardt
2. 88-Dale Jarrett
3. 10-Ricky Rudd
4. 22-Ward Burton
5. 55-Kenny Wallace
6. 20-Tony Stewart
7. 18-Bobby Labonte
8. 99-Jeff Burton
9. 4-Bobby Hamilton
10. 28-Kenny Irwin Jr.

Failed to qualify: Bobby Gerhart (No. 89), Robert Pressley (No. 77), Darrell Waltrip (No. 66), Hut Stricklin (No. 58)

• As of 2021, 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.

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

Top ten results

1. 99-Jeff Burton
2. 22-Ward Burton
3. 18-Bobby Labonte
4. 88-Dale Jarrett
5. 2-Rusty Wallace
6. 6-Mark Martin
7. 43-John Andretti
8. 40-Sterling Marlin
9. 12-Jeremy Mayfield 1 lap down
10. 4-Bobby Hamilton 1 lap down

Failed to qualify: Dave Marcis (No. 71), Rich Bickle (No. 91), Hut Stricklin (No. 58), Ed Berrier (No. 90)

• 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.
• 6th and final win of 1999 for Jeff Burton.

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

Top ten results

1. 20-Tony Stewart
2. 6-Mark Martin
3. 18-Bobby Labonte
4. 99-Jeff Burton
5. 10-Ricky Rudd
6. 88-Dale Jarrett
7. 44-Kyle Petty
8. 43-John Andretti
9. 25-Wally Dallenbach Jr.
10. 24-Jeff Gordon

Failed to qualify: Mike Wallace (No. 32)

• Tony Stewart would be the first rookie since Davey Allison in 1987 to win two races in his rookie season.
• As of 2022, this is the fastest Cup race run at Phoenix.

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

1. 20-Tony Stewart
2. 18-Bobby Labonte
3. 99-Jeff Burton
4. 6-Mark Martin
5. 88-Dale Jarrett
6. 31-Mike Skinner
7. 44-Kyle Petty
8. 3-Dale Earnhardt 1 lap down
9. 25-Wally Dallenbach Jr. 1 lap down
10. 24-Jeff Gordon 1 lap down

Failed to qualify: Dave Marcis (No. 71), Ed Berrier (No. 90), Derrike Cope (No. 41), Andy Belmont (No. 04), Bob Strait (No. 61)

• 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.

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

Top ten results

1. 18-Bobby Labonte
2. 88-Dale Jarrett
3. 12-Jeremy Mayfield
4. 6-Mark Martin
5. 99-Jeff Burton
6. 97-Chad Little
7. 10-Ricky Rudd
8. 31-Mike Skinner
9. 3-Dale Earnhardt
10. 4-Bobby Hamilton

Failed to qualify: Darrell Waltrip (No. 66), Derrike Cope (No. 15), Hut Stricklin (No. 75), Ricky Craven (No. 50), Stacy Compton (No. 9), Morgan Shepherd (No. 05)

• 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.
• After 16 straight seasons with at least one victory from 1983 to 1998, Ricky Rudd failed to keep his winning streak alive in 1999. His 16-season winning streak of at least one race came to a total of 20 wins. His best finish in the 1999 season was 3rd place twice (Goody's Headache Powder 500 and Winston 500). 16 straight seasons with at least 1 win was a NASCAR Modern Era record, a record that was tied with Rusty Wallace in 2001, and future champion Jimmie Johnson in 2017. In 2021, another future champion, Kyle Busch, became the Modern Era record holder after winning in Kansas, marking his 17th consecutive year of winning at least 1 race. Not only is he the Modern Era Record leader with 17 straight seasons, Busch is currently tied for 2nd All-Time with David Pearson (1964-1980). 18 straight seasons is the All-Time Record, which is held by Richard Petty. Petty went on to win 185 races from 1960 to 1977.
• This was the first race without Dale Earnhardt Jr and Matt Kenseth until 2012 Bank Of America 500 and 2015 AAA Texas 500.