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).
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.
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.
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.
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.
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 (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.
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.
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.
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 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.
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.
This race was run caution-free. It was therefore the fastest NASCAR Cup race at MIS, with Dale Jarrett's average speed being 173.997mph. 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.
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.
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.
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.
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]
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.
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.
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.
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.
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.
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.
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.
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.
Gallery
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.
The 2005 NASCAR Nextel Cup Series was the 57th season of professional stock car racing in the United States and the 34th modern-era Cup series. The season began on Saturday, February 12. The ten-race Chase for the Nextel Cup started with the Sylvania 300 on Sunday, September 18, and ended on Sunday, November 20, with the Ford 400.
The 2006 NASCAR Nextel Cup Series was the 58th season of professional Stock car racing in the United States and the 35th modern-era NASCAR Cup series season. It was started at Daytona International Speedway on Sunday, February 12 with the Budweiser Shootout and ended on Monday, November 20, with the Ford 400 at Homestead-Miami Speedway. The Chase for the Nextel Cup began with the Sylvania 300 on Sunday, September 17, at New Hampshire International Speedway. This was the last full-time season with the Gen 4 car.
The 2004 NASCAR Nextel Cup Series was the 56th season of professional stock car racing in the United States and the 33rd modern-era Cup series season. The season began on Saturday, February 7, and ended on Sunday, November 21. Kurt Busch, who drove a Ford for Roush Racing, was the Nextel Cup champion. It would be the last time until 2012 that the championship would be won by someone other than Tony Stewart or Jimmie Johnson.
The 2003 NASCAR Winston Cup Series was the 55th season of professional stock car racing in the United States and the 32nd modern-era Cup Series season. The season began on February 8 at the Daytona International Speedway with the Budweiser Shootout and ended on November 16 at Homestead-Miami Speedway with the Ford 400. Despite only winning one race throughout the whole season, Matt Kenseth, driving the No.17 Ford for Roush Racing, was strongly consistent following the lone win, and was crowned the Winston Cup champion. His only win came in the third race of the 36 race season. Chevrolet took home the NASCAR Manufacturers' Championship after capturing 19 wins and 264 points over second-place finisher Dodge, who had nine wins and 203 points. Ford finished the year third with seven wins and 200 points, and Pontiac finished fourth with one win and 125 points.
The 2002 NASCAR Winston Cup Series was the 54th season of professional stock car racing in the United States and the 31st modern-era Cup Series season. It began on February 10, 2002, at Daytona International Speedway, and ended on November 17, 2002, at Homestead-Miami Speedway. Tony Stewart, driving for Joe Gibbs Racing, was declared as the Winston Cup champion. Bill Elliott won the 2002 NASCAR's Most Popular Driver Award. He would win it for the 16th and final time in his career. He withdrew from the ballot after receiving the award. The NASCAR Manufacturers' Championship was captured by Ford after winning 14 events and gaining 245 points over second-place finisher Chevrolet, who had 10 wins and 211 points.
The 1990 NASCAR Winston Cup Series was the 42nd season of professional stock car racing in the United States and the 19th modern-era Cup Series. It began on Sunday, February 11, and ended on Sunday, November 18. Because of a highly controversial penalty to Mark Martin early in the season, Dale Earnhardt with Richard Childress Racing was crowned the Winston Cup champion for the fourth time, edging out Martin by 26 points.
The 1998 NASCAR Winston Cup Series was the 50th season of professional stock car racing in the United States and the 27th modern-era cup series. The season included 33 races and three exhibition races, beginning with the Daytona 500 at Daytona International Speedway and ending with the NAPA 500 at Atlanta Motor Speedway. Jeff Gordon won the Driver's Championship, the third of his career, and his third in the last four seasons.
The 2000 NASCAR Winston Cup Series was the 52nd season of professional stock car racing in the United States, and was the 29th modern-era Cup series. The season began on February 13 and ended on November 20. Joe Gibbs Racing driver Bobby Labonte was crowned champion at season's end. The NASCAR Manufacturers' Championship was won by Ford as they captured 14 wins and 234 points to better Pontiac's 11 wins and 213 points. Chevrolet finished third with nine wins and 199 points.
The 1997 NASCAR Winston Cup Series was the 49th season of professional stock car racing in the United States and the 26th modern-era NASCAR Cup series. It began on February 9 and ended on November 16. Jeff Gordon of Hendrick Motorsports won his second Cup championship at the end of the season.
The 1994 NASCAR Winston Cup Series was the 46th season of NASCAR professional stock car racing in the United States and the 23rd modern-era Cup series. The season began on Sunday, February 20, and ended on Sunday, November 13. Dale Earnhardt of Richard Childress Racing was crowned champion at season's end, winning consecutive Winston Cups for the third time in his career and tying Richard Petty for the record of most top-level NASCAR championships with seven. It was also the 7th and final NASCAR Winston Cup Series Championship for Dale Earnhardt before his death 7 years later in 2001, this was also the final season for 18-time Winston Cup winner Harry Gant.
The 1996 NASCAR Winston Cup Series was the 48th season of professional stock car racing in the United States and the 25th modern-era NASCAR Cup series. The season had been started on February 18 at Daytona International Speedway, and ended on November 10 at Atlanta Motor Speedway. The season would be remembered for Terry Labonte pulling off a massive upset and winning his second Winston Cup Championship over teammate Jeff Gordon.
The 2001 NASCAR Winston Cup Series was the 53rd season of professional stock car racing in the United States, the 30th modern-era Cup series. It began on February 11, 2001, at Daytona International Speedway and ended on November 23, 2001, at New Hampshire International Speedway. Jeff Gordon of Hendrick Motorsports was declared as the series champion for the fourth time in seven years.
The 1995 NASCAR Winston Cup Series was the 47th season of professional stock car racing in the United States and the 24th modern-era Cup series season. The season began on February 12 in Daytona Beach and concluded on November 12 at the Atlanta Motor Speedway. Jeff Gordon of Hendrick Motorsports won his first career championship.
The 1993 NASCAR Winston Cup Series was the 45th season of professional stock car racing in the United States and the 22nd modern-era Cup season. The season began on February 7 and ended on November 14. Dale Earnhardt of Richard Childress Racing won the title, the sixth of his career.
The 1989 NASCAR Winston Cup Series was the 41st season of professional stock car racing in the United States and the 18th modern-era Cup season. It began February 12 and ended November 19. Rusty Wallace of Blue Max Racing won the championship. This was the first year that every Winston Cup race had flag to flag coverage, with almost all of them being televised live.
The 1987 NASCAR Winston Cup Series was the 39th season of professional stock car racing in the United States and the 16th modern-era cup series.
The 2001 edition of The Winston was held on May 19, 2001, at Lowe's Motor Speedway in Concord, North Carolina. This was the 17th running of the event. The race is mostly remembered for the start, when rain progressed onto the track, causing cars to get loose and crash into the wall. One of the first ones to crash was Kevin Harvick, in his first appearance at the speedway. Then Jeff Gordon got sideways and wrecked after tapping Jeff Burton from behind, then Michael Waltrip wrecked Gordon, destroying his car, at which point the race was stopped. All of the drivers returned with back-up cars. At the end, Gordon came across the line and won his third All-Star race, tying Dale Earnhardt. Drivers Johnny Benson and Todd Bodine advanced from The Winston Open, with Benson winning the Open and Bodine winning the No Bull 5 Sprint race. This was the first Winston event without Darrell Waltrip and Dale Earnhardt. Waltrip retired at the end of 2000 and called the 2001 race from the booth, and Earnhardt was killed earlier in the season at the Daytona 500. Both drivers competed in the first 16 events.
The 2002 edition of The Winston was held on May 18, 2002 at Lowe's Motor Speedway in Concord, North Carolina. It featured the last multiple-segment Open where only segment winners advanced until 2015, and had a 27-car field, the largest in All-Star race history. Ryan Newman won the race and became the second driver since Michael Waltrip to win the event after coming out from the Open and the only driver from the second segment to win. Newman and Jeremy Mayfield advance to The Winston after winning the two segments of the Open races.
The 2004 Pepsi 400 was the 17th race of the 2004 NASCAR Nextel Cup Series season. It was held on July 3, 2004 at Daytona International Speedway in Daytona Beach, Florida. Jeff Gordon of Hendrick Motorsports won the race from the pole position and also led the most laps.
The 1996 edition of The Winston Select was a stock car racing competition that took place on May 18, 1996. Held at Charlotte Motor Speedway in Concord, North Carolina, the 70-lap race was an exhibition race in the 1996 NASCAR Winston Cup Series. Jeff Gordon of Hendrick Motorsports won the pole. Terry Labonte of Hendrick Motorsports led the most laps with 22 of the 70 laps. Michael Waltrip of Wood Brothers Racing became the first transferee to win the Winston Select after qualifying in the Winston Select Open.
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