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 and third place Pontiac who had 9 wins and 205 points.^[1]

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).

Manufacturer	Team	No.	Race driver	Crew chief
Chevrolet	Andy Petree Racing	33	Ken Schrader	Sammy Johns
		55	Kenny Wallace	Jimmy Elledge
	Dale Earnhardt, Inc.	1	Steve Park	Phillipe Lopez 10 Steve Hmiel 1 Paul Andrews 23
	Hendrick Motorsports	5	Terry Labonte	Andy Graves
		24	Jeff Gordon	Ray Evernham 27 Brian Whitesell 7
		25	Wally Dallenbach Jr.	Tony Furr
	Joe Bessey Motorsports	60	Geoff Bodine	Jim Long
	Larry Hedrick Motorsports	41	David Green 25	Tim Brewer 1 Mike Hill 2 Donnie Disharoon 31
			Dick Trickle 4
			Derrike Cope 4
			Gary Bradberry 1
	Marcis Auto Racing	71	Dave Marcis 33	Bob Marcis
			R. K. Smith 1
	Mattei Motorsports	7	Michael Waltrip	Bobby Kennedy
	Morgan-McClure Motorsports	4	Bobby Hamilton	Charlie Pressley 1 Gary DeHart 33
	Richard Childress Racing	3	Dale Earnhardt	Kevin Hamlin
		31	Mike Skinner	Larry McReynolds
	Team SABCO	40	Sterling Marlin	Corrie Stott 11 Tony Glover 1 Scott Eggleston 22
		42	Joe Nemechek	Scott Eggleston 12 Tony Glover 22
Ford	Elliott-Marino Racing Bill Elliott Racing	94	Bill Elliott	Joe Garone 6 Jerry Pitts 4 Wayne Orme 23 Ernie Elliott 1
	Brett Bodine Racing	11	Brett Bodine	Gere Kennon 20 Rick Gay 14
	Butch Mock Motorsports Galaxy Motorsports	75	Ted Musgrave 33	Jon Wolfe 20 Greg Ely 14
			Hut Stricklin 1
	Yarborough Burdette Motorsports	98	Rick Mast	Michael McSwain 10 Jerry Pitts 3 Mark Tutor 15 Dan Glauz 6
	Haas-Carter Motorsports	23	Jimmy Spencer	Donnie Wingo
		66	Darrell Waltrip	Donnie Disharoon 3 Joe Snyder 1 Travis Carter 5 Mark Tutor 6 Phillippe Lopez 18
	Jasper Motorsports	77	Robert Pressley	Newt Moore 11 Charley Pressley 23
	Melling Racing	9	Jerry Nadeau 22	Jeff Buice 13 Newt Moore 17 Kevin Cram 4
			Steve Grissom 3
			Rich Bickle 5
			Stacy Compton 4
	Penske-Kranefuss Racing	2	Rusty Wallace	Robin Pemberton
		12	Jeremy Mayfield	Paul Andrews 11 Peter Sospenzo 23
	Robert Yates Racing	28	Kenny Irwin Jr.	Doug Richert 30 Ray Fox 4
		88	Dale Jarrett	Todd Parrott
	Roush Racing	6	Mark Martin	Jimmy Fennig
		16	Kevin Lepage	James Ince 7 Tommy Morgan 1 Skip Eyler 11 Pat Tryson 30
		26	Johnny Benson	Bobby Leslie 10 Pat Tryson 13 Tommy Morgan 11
		97	Chad Little	Jeff Hammond
		99	Jeff Burton	Frank Stoddard
	Rudd Performance Motorsports	10	Ricky Rudd	Bill Ingle 4 Dan Stillman 6 Michael McSwain 24
	Wood Brothers Racing	21	Elliott Sadler (R)	Mike Beam
Pontiac	Bahari Racing Eel River Racing	30	Derrike Cope 22	Dan Glauz 19 Barry Dodson 15
			Todd Bodine 9
			Mike Bliss 2
			Buckshot Jones (R) 1
	Bill Davis Racing	22	Ward Burton	Tommy Baldwin Jr.
	Joe Gibbs Racing	18	Bobby Labonte	Jimmy Makar
		20	Tony Stewart (R)	Greg Zipadelli
	MB2 Motorsports	36	Ernie Irvan 21	Ryan Pemberton
			Dick Trickle 1
			Jerry Nadeau 12
	Petty Enterprises	43	John Andretti	Robbie Loomis
		44	Kyle Petty	Doug Hewitt
	Tyler Jet Motorsports	45	Rich Bickle 24	Phil Hammer 7 Bill Ingle 3 James Ince 24
			Jack Sprague 1
			David Green 9

Manufacturer	Team	No.	Race driver	Crew chief	Round(s)
Chevrolet	Barkdoll Racing	73	Ken Bouchard		1
	Dale Earnhardt, Inc.	8	Dale Earnhardt Jr.	Tony Eury Sr.	5
	Highland Timber Racing	08	Harris DeVane		1
	Fast Track Racing	48	Glen Morgan		1
	AC Motorsports	89	Austin Cameron		2
	Gerhart Racing		Bobby Gerhart		1
	LJ Racing	91	Steve Grissom	Skip Eyler 8 Joe Falk 1 Nicholas Short 17	4
			Dick Trickle		12
			Hut Stricklin		1
			Morgan Shepherd		1
			Jack Baldwin		1
			Tom Baldwin		1
			Derrike Cope		2
			Tim Fedewa		1
			Andy Hillenburg		2
			Rich Bickle		1
	Marcis Auto Racing	72	Jim Sauter		1
	Ted Christopher Racing	13	Ted Christopher	Kevin Cram	1
	Metcalf Motorsports	70	John Metcalf		1
	Midwest Transit Racing	50	Dan Pardus (R)	John McQueen 3 Jay Born 2 John Monsam13	3
			Billy Standridge		1
			Ron Hornaday Jr.		1
			Ricky Craven		13
	NEMCO Motorsports	87	Ron Fellows	Brian Pattie	1
	Petty-Huggins Racing	84	Stanton Barrett (R)		1
			Ken Bouchard		3
	Team SABCO	01	Jeff Green	Bob Temple	2
			Steve Grissom		2
			Ron Hornaday Jr.		2
	T.R.I.X. Racing	79	Norm Benning	Ted Walters	1
			Andy Belmont		1
Ford					1
	Elliott-Marino Racing	13	Dick Trickle	Wayne Orme	1
	Bud Moore Engineering Fenley-Moore Motorsports	15	Jeff Green		1
			Derrike Cope		2
		62	Lance Hooper		1
	CSG Racing	59	Mark Gibson	Tony Gibson	1
	Zali Racing	92	Morgan Shepherd	Brian Bass	1
	Donlavey Racing	90	Mike Wallace	Greg Connor 19 Junie Donlavey 7	1
			Mike Harmon (R)		1
			Morgan Shepherd		3
			Stanton Barrett (R)		9
			Ed Berrier		7
			Loy Allen Jr.		1
			Hut Stricklin		6
	Hover Motorsports	80	Andy Hillenburg		1
			Gary Bradberry		2
	Irvan-Simo Racing	14	Randy LaJoie	Jerry Baxter	3
			Boris Said		5
			Buckshot Jones (R)		1
	Jenn West Motorsports	38	Butch Gilliland		3
	Mansion Motorsports	85	Carl Long		2
	Meacham Racing	04	Andy Belmont		1
	Phoenix Air Racing	61	David Murry	Bob Bissinger	2
			Bob Strait	Donnie Straight	2
	Pinnacle Motorsports	81	Morgan Shepherd		1
	Roehrig Motorsports	19	Tom Hubert	Mike Bodick	1
	Ron Burns Racing	68	Ron Burns		1
	Roush Racing	17	Matt Kenseth	Robbie Reiser	5
	SBIII Motorsports	58	Ricky Craven	Mike Hillman 25 Jerry Pitts 6	13
			Loy Allen Jr.		3
			Sean Woodside		1
			Hut Stricklin		14
	Standridge Motorsports	47	Billy Standridge	Dave Smith	1
	Triad Motorsports	78	Gary Bradberry	Hut Stricklin	1
	Ultra Motorsports	32	Mike Wallace	Tim Brewer	3
Pontiac	Bill Davis Racing	93	Dave Blaney	Gil Martin	5
	Buckshot Racing	00	Buckshot Jones (R)	Tony Barclay	17
	Shepherd Racing	05	Morgan Shepherd		4
	Golden Gate Racing Team	96	Steve Portenga		1
	Joyner-Kersee Racing	19	Tom Hubert	Mike Bodick	2
			Paul Gentilozzi		1
	Midgley Motorsports	09	Mike Borkowski		1

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

No.	Race Title	Track	Date
	Bud Shootout Qualifier	Daytona International Speedway, Daytona Beach	February 7
	Bud Shootout
	Gatorade 125s		February 11
1	Daytona 500		February 14
2	Dura Lube/Big K 400	North Carolina Speedway, Rockingham	February 21
3	Las Vegas 400	Las Vegas Motor Speedway, Las Vegas	March 7
4	Cracker Barrel 500	Atlanta Motor Speedway, Hampton	March 14
5	TranSouth Financial 400	Darlington Raceway, Darlington	March 21
6	Primestar 500	Texas Motor Speedway, Fort Worth	March 28
7	Food City 500	Bristol Motor Speedway, Bristol	April 11
8	Goody's Body Pain 500	Martinsville Speedway, Ridgeway	April 18
9	DieHard 500	Talladega Superspeedway, Talladega	April 25
10	California 500 presented by NAPA	California Speedway, Fontana	May 2
11	Pontiac Excitement 400	Richmond International Raceway, Richmond	May 15
	No Bull 25 Shootout	Lowe's Motor Speedway, Concord	May 22
	Winston Open
	The Winston
12	Coca-Cola 600		May 30
13	MBNA Platinum 400	Dover Downs International Speedway, Dover	June 6
14	Kmart 400	Michigan Speedway, Brooklyn	June 13
15	Pocono 500	Pocono Raceway, Long Pond	June 20
16	Save Mart/Kragen 350	Sears Point Raceway, Sonoma	June 27
17	Pepsi 400	Daytona International Speedway, Daytona Beach	July 3
18	Jiffy Lube 300	New Hampshire International Speedway, Loudon	July 11
19	Pennsylvania 500	Pocono Raceway, Long Pond	July 25
20	Brickyard 400	Indianapolis Motor Speedway, Speedway	August 7
21	Frontier at The Glen	Watkins Glen International, Watkins Glen	August 15
22	Pepsi 400 presented by Meijer	Michigan Speedway, Brooklyn	August 22
23	Goody's Headache Powder 500	Bristol Motor Speedway, Bristol	August 28
24	The 50th Pepsi Southern 500	Darlington Raceway, Darlington	September 5
25	Exide NASCAR Select Batteries 400	Richmond International Raceway, Richmond	September 11
26	Dura Lube/Kmart 300	New Hampshire International Speedway, Loudon	September 19
27	MBNA Gold 400	Dover Downs International Speedway, Dover	September 26
28	NAPA Autocare 500	Martinsville Speedway, Ridgeway	October 3
29	UAW-GM Quality 500	Lowe's Motor Speedway, Concord	October 11
30	Winston 500	Talladega Superspeedway, Talladega	October 17
31	Pop Secret Microwave Popcorn 400	North Carolina Speedway, Rockingham	October 24
32	Checker Auto Parts/Dura Lube 500	Phoenix International Raceway, Phoenix	November 7
33	Pennzoil 400 presented by Kmart	Homestead-Miami Speedway, Homestead	November 14
34	NAPA 500	Atlanta Motor Speedway, Hampton	November 21

No.	Race	Pole position	Most laps led	Winning driver	Manufacturer
	Bud Shootout Qualifier	Geoff Bodine	Mike Skinner	Mike Skinner	Chevrolet
	Bud Shootout	Rusty Wallace	Mark Martin	Mark Martin	Ford
	Gatorade 125 No. 1	Jeff Gordon	Jeff Gordon	Bobby Labonte	Pontiac
	Gatorade 125 No. 2	Tony Stewart	Dale Earnhardt	Dale Earnhardt	Chevrolet
1	Daytona 500	Jeff Gordon	Rusty Wallace	Jeff Gordon	Chevrolet
2	Dura Lube/Big K 400	Ricky Rudd	Jeff Burton	Mark Martin	Ford
3	Las Vegas 400	Bobby Labonte	Jeff Burton	Jeff Burton	Ford
4	Cracker Barrel 500	Bobby Labonte	Jeff Gordon	Jeff Gordon	Chevrolet
5	TranSouth Financial 400	Jeff Gordon	Jeff Burton	Jeff Burton	Ford
6	Primestar 500	Kenny Irwin Jr.	Terry Labonte	Terry Labonte	Chevrolet
7	Food City 500	Rusty Wallace	Rusty Wallace	Rusty Wallace	Ford
8	Goody's Body Pain 500	Tony Stewart	Rusty Wallace	John Andretti	Pontiac
9	DieHard 500	Ken Schrader	Dale Earnhardt	Dale Earnhardt	Chevrolet
10	California 500 pres. by NAPA	Jeff Burton	Jeff Gordon	Jeff Gordon	Chevrolet
11	Pontiac Excitement 400	Jeff Gordon	Jeff Burton	Dale Jarrett	Ford
	No Bull 25 Race 1	Steve Park	Mike Skinner	Mike Skinner	Chevrolet
	No Bull 25 Race 2	Tony Stewart	Tony Stewart	Tony Stewart	Pontiac
	Winston Open	Mike Skinner	Tony Stewart	Tony Stewart	Pontiac
	The Winston	Bobby Labonte	Jeff Gordon	Terry Labonte	Chevrolet
12	Coca-Cola 600	Bobby Labonte	Jeff Burton	Jeff Burton	Ford
13	MBNA Platinum 400	Bobby Labonte	Tony Stewart	Bobby Labonte	Pontiac
14	Kmart 400 pres. by Castrol Super Clean	Jeff Gordon	Dale Jarrett	Dale Jarrett	Ford
15	Pocono 500	Sterling Marlin	Dale Jarrett	Bobby Labonte	Pontiac
16	Save Mart/Kragen 350	Jeff Gordon	Jeff Gordon	Jeff Gordon	Chevrolet
17	Pepsi 400	Joe Nemechek	Rusty Wallace	Dale Jarrett	Ford
18	Jiffy Lube 300	Jeff Gordon	Tony Stewart	Jeff Burton	Ford
19	Pennsylvania 500	Mike Skinner	Mike Skinner	Bobby Labonte	Pontiac
20	Brickyard 400	Jeff Gordon	Dale Jarrett	Dale Jarrett	Chevrolet
21	Frontier at the Glen	Rusty Wallace	Jeff Gordon	Jeff Gordon	Chevrolet
22	Pepsi 400 pres. by Meijer	Ward Burton	Jeff Gordon	Bobby Labonte	Pontiac
23	Goody's Headache Powder 500	Tony Stewart	Tony Stewart	Dale Earnhardt	Chevrolet
24	The 50th Pepsi Southern 500	Kenny Irwin Jr.	Jeff Burton	Jeff Burton	Ford
25	Exide NASCAR Select Batteries 400	Mike Skinner	Tony Stewart	Tony Stewart	Pontiac
26	Dura Lube/Kmart 300	Rusty Wallace	Rusty Wallace	Joe Nemechek	Chevrolet
27	MBNA Gold 400	Rusty Wallace	Mark Martin	Mark Martin	Ford
28	NAPA Autocare 500	Joe Nemechek	Mike Skinner	Jeff Gordon	Chevrolet
29	UAW-GM Quality 500	Bobby Labonte	Bobby Labonte	Jeff Gordon	Chevrolet
30	Winston 500	Joe Nemechek	Jeff Gordon	Dale Earnhardt	Chevrolet
31	Pop Secret Microwave Popcorn 400	Mark Martin	Dale Jarrett	Jeff Burton	Ford
32	Checker Auto Parts/Dura Lube 500	John Andretti	Tony Stewart	Tony Stewart	Pontiac
33	Pennzoil 400 pres. by Kmart	David Green	Bobby Labonte	Tony Stewart	Pontiac
34	NAPA 500	Kevin Lepage	Bobby Labonte	Bobby Labonte	Pontiac

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 2024, 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 2024, 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 15 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 No. 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 2024, 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 2024, 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 2024, 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 2024, 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.

(key) Bold - Pole position awarded by time. Italics - Pole position set by owner's points standings. *- Most laps led.

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 (R)	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
12	Terry Labonte	38	7	8	13	11	1*	13	15	39	9	26	11	17	23	16	29	10	11	6	11	11	26	8	17	43	31	27	40	21	34	14	28	31	40	3580
13	Bobby Hamilton	29	9	24	12	7	29	18	33	31	30	4	13	21	31	10	11	8	16	17	38	22	35	41	7	7	11	30	30	22	9	10	23	25	10	3564
14	Steve Park	34	26	16	32	12	32	23	25	37	24	34	42	16	6	13	42	42	12	8	15	12	20	31	10	16	15	9	12	10	14	15	15	19	12	3481
15	Ken Schrader	6	11	18	26	43	17	20	9	6	14	14	7	41	13	27	39	20	35	34	18	17	25	10	9	21	12	26	21	23	25	30	14	29	19	3479
16	Sterling Marlin	32	37	15	18	16	9	14	13	25	16	18	40	29	22	4	25	12	34	28	16	33	15	7	40	4	21	38	11	29	22	8	40	17	31	3397
17	John Andretti	43	19	12	28	9	38	4	1	9	17	39	19	13	8	28	3	19	18	42	37	29	10	40	18	9	41	41	43	17	32	7	8	16	33	3394
18	Wally Dallenbach Jr.	12	17	13	39	38	23	30	18	20	8	20	21	20	14	39	41	26	7	5	14	7	23	28	21	28	22	15	22	33	35	39	9	9	23	3367
19	Kenny Irwin Jr.	3	23	41	23	35	15	11	36	35	13	40	15	10	11	18	22	14	26	43	13	26	34	24	31	5	10	10	39	15	10	13	21	33	29	3338
20	Jimmy Spencer	41	25	26	17	20	28	17	16	16	36	29	38	23	43	14	5	27	9	20	26	16	8	2	15	37	24	14	17	28	24	20	17	20	42	3312
21	Bill Elliott	27	15	37	15	14	21	25	30	10	19	12	14	12	41	31	13	23	5	39	23	28	19	36	11	36	19	33	20	11	20	33	35	24	22	3246
22	Kenny Wallace	42	13	40	29	33	39	16	6	7	27	41	12	39	21	25	14	15	2	37	39	19	27	11	35	12	34	43	5	30	5	16	18	15	34	3210
23	Chad Little	9	21	14	9	28	13	24	17	42	22	35	24	28	28	32	16	29	24	22	43	14	6	30	20	42	28	7	31	18	36	21	16	39	6	3193
24	Elliott Sadler (R)	40	38	33	31	36	10	26	28	29	21	23	17	27	36	20	18	22	20	21	21	18	11	35	14	17	14	12	25	26	21	18	27	18	16	3191
25	Kevin Lepage	13	42	21	19	22	41	35	21	12	18	13	26	26	29	17	32	30	22	24	30	25	39	22	5	26	26	13	27	9	18	22	24	26	17	3185
26	Kyle Petty	7	43	DNQ	43	31	DNQ	8	10	13	26	7	30	32	27	19	8	36	41	16	41	8	31	29	28	15	33	20	7	32	19	23	7	7	24	3103
27	Geoff Bodine	39	8	32	38	17	36	28	38	17	37	17	41	15	20	33	28	28	32	13	25	35	17	13	24	23	35	24	3	20	23	31	22	11	18	3053
28	Johnny Benson	17	16	38	22	18	11	29	35	30	43	28	18	7	19	30	26	24	17	14	19	38	21	33	32	22	7	18	28	16	42	28	31	35	39	3012
29	Michael Waltrip	5	20	22	10	21	14	12	39	18	23	22	37	42	15	37	10	39	19	12	27	21	13	37	41	38	38	19	33	14	39	27	33	36	36	2974
30	Joe Nemechek	36	24	35	14	19	33	36	37	34	40	6	32	25	34	42	19	16	37	29	22	30	22	19	6	20	1	35	38	13	30	26	19	21	32	2956
31	Ricky Rudd	30	30	43	25	27	19	38	29	19	41	36	28	14	38	15	38	13	27	27	9	32	38	3	34	27	42	37	18	38	3	19	5	41	7	2922
32	Rick Mast	10	35	19	16	13	30	19	42	24	31	16	34	34	37	12	23	32	30	19	36	23	12	21	30	41	9	34	29	25	26	38	36	28	41	2845
33	Ted Musgrave	15	40	DNQ	24	29	31	7	40	28	29	11	23	24	25	11	20	35	25	33	35	27	41	16	38	8	23	28	19	31	29	32	29	42		2689
34	Jerry Nadeau	11	31	31	27	40	24	42	32	8	20	21	20	30	26	23	34	37	36	38	31	5	29	20	43	18	32	16	26	34	40	37	37	38	20	2686
35	Brett Bodine	22	33	20	33	30	18	22	14	43	28	38	22	37	30	26	31	34	31	26	DNQ	40	DNQ	12	26	31	29	29	42	27	31	43	42	40	30	2351
36	David Green	DNQ	18	27	21	42	26	33	26	33	25	43	27	18	35	38	36	33	DNQ	41	20	37	32	25	42	33	40	42	36	42	17	24	12	22	21	2320
37	Darrell Waltrip	21	27	25	20	41	25	32	12	26	15	25	43	DNQ	39	34	12	38	33	25	42	15	DNQ	14	29	32	DNQ	DNQ	23	DNQ	DNQ	34	26	43	DNQ	2158
38	Rich Bickle	33	DNQ	23	30	DNQ	12	DNQ	11	14	32	10	25	33	24	24	21	18	14	7	DNQ	36	28	DNQ	23		20	36	37	39	41	DNQ				2149
39	Robert Pressley	19	14	DNQ	DNQ	15	20	40	23	22	39	27	35	40	42	35	40	DNQ	DNQ	23	17	DNQ	42	43	25	39	30	23	35	24	DNQ	29	38	37	27	2050
40	Ernie Irvan	14	29	6	7	24	37	43	22	40	35	33	36	35	7	8	30	9	21	11	24	41	QL													1915
41	Ricky Craven	26	22	39	42	37	27	41	43	27	34	19	DNQ	31				43	13		34		30	42			43	40	24	43		41	30	32	DNQ	1513
42	Dave Marcis	16	34	DNQ	34	DNQ	DNQ	34	DNQ	23	33	DNQ	DNQ	38	DNQ	41		31	DNQ	30	40	DNQ	33	34	33	DNQ	25	39	34	DNQ	38	DNQ	34	DNQ	28	1324
43	Hut Stricklin										DNQ	DNQ	33	DNQ	DNQ	DNQ		DNQ	39	15	33	DNQ	9	27	27	DNQ	16	25	14	DNQ	DNQ	DNQ			DNQ	918
44	Derrike Cope	18	DNQ	34	41	DNQ	22	DNQ	34	DNQ	42	42	DNQ	36	32	DNQ	37	DNQ	DNQ	DNQ	32	DNQ	DNQ				DNQ	DNQ		35	37	25	43	DNQ	DNQ	915
45	Buckshot Jones (R)	DNQ	DNQ	29	37	34	35	39	DNQ	21	DNQ	DNQ	29	DNQ	DNQ	Wth		41			DNQ									DNQ	27				26	676
46	Todd Bodine																							15	DNQ	19	39	DNQ		36			25	27	43	529
47	Dick Trickle	DNQ				26	DNQ	31	31	DNQ		32	DNQ	43	Wth	40			29		DNQ		40	DNQ		QL	DNQ	DNQ	DNQ	41						528
48	Dale Earnhardt Jr.												16						43				24			10									14	500
49	Matt Kenseth					QL																	14		37			4		40		35				434
50	Steve Grissom	DNQ	36	42	DNQ																DNQ			39	39	30					28					336
51	Dave Blaney														33				40		28													23	37	332
52	Ed Berrier					39																						31		DNQ	33	DNQ		DNQ	25	268
53	Mike Wallace	23																			DNQ					24							DNQ			185
54	Ron Fellows																					2														174
55	Stacy Compton																															36	39	30	DNQ	174
56	Stanton Barrett	DNQ		30			DNQ	DNQ										Wth		31	DNQ		DNQ		DNQ	DNQ										143
57	Tom Hubert			28													33						DNQ													143
58	Mike Bliss																												32			42				104
59	Boris Said										DNQ						DNQ				DNQ	42												34		103
60	Jeff Green	DNQ					Wth						DNQ			21																				100
61	Randy LaJoie						40						DNQ														37									95
62	Loy Allen Jr.									DNQ					40	DNQ	QL	40																		86
63	Ron Hornaday Jr.			DNQ																						29			DNQ							76
64	Ted Christopher																					31														70
65	Morgan Shepherd	DNQ	32	DNQ	DNQ				DNQ				DNQ							DNQ	DNQ								DNQ						DNQ	67
66	Gary Bradberry	DNQ	Wth	Wth	Wth																DNQ									DNQ					35	58
67	David Murry																Wth					39														46
68	Andy Hillenburg	DNQ																												DNQ	43					34
69	Butch Gilliland			DNQ							DNQ						43																			34
70	Mark Gibson	DNQ
71	Jim Sauter	DNQ
72	Norm Benning	DNQ
73	Glen Morgan	DNQ
74	Billy Standridge	DNQ	DNQ
75	Dan Pardus (R)	DNQ								DNQ			DNQ
76	Ken Bouchard	DNQ					Wth			DNQ								DNQ
77	Ron Burns			DNQ
78	Carl Long							Wth					DNQ
79	R. K. Smith																DNQ
80	Austin Cameron			Wth													DNQ
81	Sean Woodside																DNQ
82	John Metcalf																DNQ
83	Mike Borkowski																DNQ
84	Steve Portenga																DNQ
85	Lance Hooper																				DNQ
86	Bob Strait																				DNQ													DNQ
87	Paul Gentilozzi																					DNQ
88	Jack Baldwin																					DNQ
89	Jack Sprague																									DNQ
90	Tom Baldwin																									DNQ
91	Andy Belmont																										DNQ	DNQ						DNQ
92	Tim Fedewa																												DNQ
93	Bobby Gerhart																														DNQ
94	Harris DeVane				Wth
95	Érik Comas																Wth
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

The 1999 Rookie of the Year battle was expected to be one of the most competitive in years. However, it ended up proving to be 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.

• 
  1999 NASCAR Winston Cup champion Dale Jarrett waves to the fans before the 2007 Sharpie 500
• 
  Bobby Labonte finished second behind Jarrett by 201 points.
• 
  Mark Martin (seen here in 2012 driving for Michael Waltrip Racing) finished third in the championship.
• 
  Tony Stewart (seen here in 2007) had an impressive rookie season, winning three races along with the Rookie of the Year award, and finished fourth in the final point standings.

• 1999 NASCAR Busch Series
• 1999 NASCAR Craftsman Truck Series

• Winston Cup Standings and Statistics for 1999 Archived February 24, 2009, at the Wayback Machine