1994 was Burton's rookie year in the Winston Cup Series. He drove the #8 Raybestos Ford for the Stavola Brothers team. After five races, he reached a season-high 14th place in the overall standings, but by the end of the year he dropped to 24th. He had a season-high fourth place finish on the way to earning 1994
NASCAR Rookie Of The Year . He was one of a record-high ten rookies eligible for the award that year, besting a class that included future Cup stars
Joe Nemechek ,
Jeremy Mayfield ,
John Andretti , and older brother Ward. The next year, in
1995 , Burton had 1 top-5, along with a 9th place finish. He also missed three races and finished 32nd in points.
In
1996 , Burton left the Stavola Brothers for
Roush Racing . Driving the #99 Exide Batteries Ford for his new team, he finished 13th overall in the season standings despite failing to qualify for the
Purolator 500 in March. His career hit a peak from
1997 to
2000 , as he never finished lower than 5th in the points standings. He achieved his first career win in 1997, finishing first in the Interstate Batteries 500 at
Texas Motor Speedway , and would go on to win 14 more races during the four-year run. In
1999 , Burton won a career-high six races, including the
Jiffy Lube 300 for a third straight year, which would lead to a fifth-place finish in points. His best points finish was in 2000, when he finished 3rd, 294 points behind champion
Bobby Labonte . During that year, on September 17th, he led the
Dura Lube 300 Sponsored By Kmart at
New Hampshire International Speedway wire-to-wire, becoming the first Cup driver to lead every lap in one race since
Cale Yarborough did so at a
1978 race in
Nashville Speedway USA . The following year, in
2001 , Burton won another two races, upping his career total to 17, as he finished tenth in points.
In
2002 and
2003 , he finished 12th and combined for 8 top-5s and 25 top-10s, but failed to win a race in either year. Rumors began to arise that Burton would be leaving Roush Racing. This finally happened in mid-
2004 when, just before the
Sirius At The Glen , Burton signed a three-year contract with
Richard Childress Racing (RCR), leaving Roush after eight and a half years with the team. He would drive the #30 America Online Chevrolet for the rest of the season. Before the change, Burton had an average finish of 20.8 and was 23rd in points. In the 13 races after he changed teams, though, the same stats were improved to 16.6 and 18th. During the offseason, Burton and his team remained with RCR but were switched to the #31 Cingular Wireless Chevy, replacing
Robby Gordon .
Burton won the pole for the
2006 Daytona 500 , his first in the NEXTEL Cup since the 2000 season. He also won a Busch Series race at
Atlanta Motor Speedway , ending a four-year winless streak.