Dale Jarrett's steady championship, Tony Stewart's three rookie wins and a run of unusual finishes made the final Winston Cup season of the twentieth century.
Dale Jarrett's 1999 Winston Cup title came in a season that ran from February 7 to November 21. Jarrett of Robert Yates Racing clinched at Homestead with a 211-point lead, while Ford took the manufacturers' championship with 13 wins. Tony Stewart's three rookie wins stood out in a season of narrow finishes.
The 1999 NASCAR Winston Cup Series ran from February 7 to November 21 and was the last season of the 1990s and of the twentieth century. Dale Jarrett of Robert Yates Racing took the championship and locked it up with a race to spare at Homestead. Ford also won the manufacturers' title, with 13 wins to Chevrolet's 12.
How did Dale Jarrett win the title?
Jarrett won the championship through consistency rather than a long run of victories. He took the points lead at Richmond in May and held it to the end. He finished 29 times in the top ten across 34 races, a record that stood until 2007.
Jarrett's season was built on finishing rather than winning outright. With 29 top-ten results in 34 races, he rarely lost ground, and that steadiness was enough to hold off rivals who won more races than he did.
The turning point in May came at Richmond, where Jarrett won the Pontiac Excitement 400 while the points leader, Jeff Burton, finished 37th. Burton had been the points leader going into that race, so the swing was immediate. Jarrett moved to the top of the standings that afternoon and never gave it back.
Jarrett's four wins in 1999 came at Richmond, Michigan, Daytona and Indianapolis. The Brickyard 400 win on August 7 was a form of redemption, because a year earlier he had run out of fuel while in contention there. It was also the last Ford victory in that race until Brad Keselowski's in 2018.
Jarrett's Michigan win on June 13 came in a race run without a single caution, and it was the fastest Cup race ever run at that track.
The championship was never a runaway. The gap moved as the season went on, and by the Pennzoil 400 at Homestead Jarrett held a 211-point lead over Bobby Labonte. The maximum for a single race under the Latford points system was 185, so the lead was enough to clinch the title before the finale at Atlanta.
Dale Jarrett's steady control and Tony Stewart's three rookie wins closed out the twentieth century's last Winston Cup season.
Who challenged Jarrett for the title?
Bobby Labonte was the main challenger and finished second in the standings. Jeff Gordon and Jeff Burton were also in contention for stretches of the year, but neither could hold the lead through the autumn, and the NAPA 500 finale gave Labonte his last realistic chance.
Gordon's season was strong by any measure. He won the Daytona 500 from the pole and extended his run of seasons with seven or more wins to five in a row, a modern-era record. A blown engine at North Carolina Speedway in February set back his early points total. His March win at Atlanta was his 35th victory in 100 straight races, a streak that dated back to Richmond in March 1996.
Gordon also took the Frontier at The Glen on August 15, his third in a row at Watkins Glen, which extended a road-course run he had built over several seasons. Ron Fellows took second, the best finish of his career, and the race was the 47th and final win of Ray Evernham's crew-chief career.
Jeff Burton's wins came at Las Vegas, Darlington, Charlotte, New Hampshire, Darlington again in September and North Carolina Speedway's Pop Secret 400 in October. He was the driver who collected the million-dollar bonus twice during the year.
Bobby Labonte also had a strong summer. He won the Pocono 500 in June and the Pennsylvania 500 in July, a rare sweep of both Pocono races in one season.
Labonte's final push came in the last race. He won the NAPA 500 at Atlanta after starting 37th on a provisional, but Jarrett's lead was already large enough to hold, and he had held the points lead since May. Jarrett himself led laps at Atlanta and finished second behind Labonte.
Terry Labonte, meanwhile, won The Winston all-star race at Lowe's Motor Speedway in May. It was his second victory in that event and his first since 1988, and he led the most laps on the way.
Why did Tony Stewart's rookie season stand out?
Tony Stewart won three races as a rookie and finished fourth in the championship. His first victory came at Richmond in September, where he led 333 of the 400 laps, making him the first newcomer to win a points race since Davey Allison in 1987.
Stewart's back-to-back wins at Phoenix on November 7 and Homestead on November 14 were a rare feat for a newcomer in the modern era. His third victory of the year closed the season.
The rookie award was a foregone conclusion. Elliott Sadler had been the favourite before the season, but he managed only one top-ten finish, and he was the only other rookie to run every race. Stewart's wins settled the contest well before the finale.
Other newcomers struggled. Buckshot Jones cut back his programme after a string of failed qualifying attempts and retirements. Stanton Barrett started with his own team, then moved to another and made only two starts, and Dan Pardus failed to qualify and was let go after the Coca-Cola 600.
The team side changed as well. Ray Evernham left Hendrick Motorsports in October to run Dodge's comeback effort in NASCAR for 2001, and Brian Whitesell took over as Jeff Gordon's crew chief for the rest of the season.
Which races produced the strangest finishes?
A few finishes stood out for their odd circumstances. Jeff Burton won at Darlington in March after rain stopped the race, while Dale Earnhardt was booed in victory lane at Bristol in August after a last-lap spin that took out the leader.
At Darlington the race never resumed once the rain arrived. Burton was leading when the showers stopped the race after a multi-car wreck, and he drove his damaged car across the line for the win. Gordon, who had been running second, was caught up in the same wreck and still finished third.
At Bristol on August 28, Earnhardt spun the leader, Terry Labonte, on the final lap. Labonte collected Ricky Rudd and Tony Stewart, and the crowd booed Earnhardt as he pulled into the winner's spot. He had started from 26th, the lowest starting position for a winner in that race.
The Pepsi Southern 500 at Darlington on September 5 was also halted by rain, on lap 270. In the same weekend, Ernie Irvan announced his retirement because of injuries from a crash at Michigan the previous month, and his final Winston Cup start had come earlier at The Glen.
Jeff Burton's Pop Secret 400 win at North Carolina Speedway in October was the third time that season the Burton brothers finished first and second, and Jeff beat Ward in all three of those races.
What did the new television deal mean?
NASCAR announced in December 1999 that the Winston Cup Series would move to a new set of networks from February 2001. FOX and FX would carry the races alongside NBC and TBS, with TBS later replaced by TNT. The old arrangements remained in place through the 2000 season.
The announcement meant that several long-standing broadcast partners would leave the series after 2000, which made 1999 one of the final seasons under the old arrangements.
Selected race results
| Date | Race | Track | Winner | Notable detail |
|---|---|---|---|---|
| February 14 | Daytona 500 | Daytona International Speedway | Jeff Gordon | First pole winner there since 1987 |
| March 7 | Las Vegas 400 | Las Vegas Motor Speedway | Jeff Burton | Burton brothers led 182 of 267 laps |
| March 21 | TranSouth Financial 400 | Darlington Raceway | Jeff Burton | Rain stopped the race |
| May 15 | Pontiac Excitement 400 | Richmond International Raceway | Dale Jarrett | Jarrett took the points lead |
| May 22 | The Winston | Lowe's Motor Speedway | Terry Labonte | Second Winston victory |
| June 6 | MBNA Platinum 400 | Dover Downs International Speedway | Bobby Labonte | Waltrip failed to qualify |
| August 7 | Brickyard 400 | Indianapolis Motor Speedway | Dale Jarrett | Redemption after a fuel problem in 1998 |
| August 28 | Goody's Headache Powder 500 | Bristol Motor Speedway | Dale Earnhardt | Booed in victory lane |
| September 5 | Pepsi Southern 500 | Darlington Raceway | Jeff Burton | Race halted on lap 270 |
| September 11 | Exide NASCAR Select Batteries 400 | Richmond International Raceway | Tony Stewart | Led 333 of 400 laps |
| November 7 | Checker Auto Parts/Dura Lube 500 | Phoenix International Raceway | Tony Stewart | Second win of the season |
| November 21 | NAPA 500 | Atlanta Motor Speedway | Bobby Labonte | Started 37th on a provisional |
How did the No Bull 5 bonus work in 1999?
The Winston No Bull 5 program paid a bonus of one million dollars to a driver who won one of its designated races. Gordon collected the first bonus at the Daytona 500 in February, and Jeff Burton collected it at Charlotte in May and at Darlington in September.
Earnhardt's Winston 500 win at Talladega in October was the final No Bull 5 race of 1999. Five drivers at the top of that finishing order were in line for the bonus at the Daytona 500 the following February.
The Talladega win was also a season sweep at that track. Earnhardt had completed one in 1990 as well, and as of 2024, he is the only driver to have swept the Talladega races twice.
What happened to Ricky Rudd's winning streak?
Ricky Rudd finished the year without a win, which ended a streak of 16 consecutive race-winning seasons. The all-time record of 18 seasons was held by Richard Petty, and Rudd was two seasons short of matching it. His best finishes in 1999 were two third-place results.
Rudd's own team, Rudd Performance Motorsports, closed after the Atlanta finale when it lost its primary sponsor. Rudd moved to Robert Yates Racing for 2000, and the closing race marked his last start as an owner-driver.
