1995-2000
At the end of the 1994 season, Labonte departed to replace Dale Jarrett as the driver of the #18 Interstate Batteries Chevrolet for Joe Gibbs Racing. Bobby would pick up his first career win at the Coca Cola 600 in 1995. He would also go on and sweep the races at Michigan, and finish 10th in the standings.
In 1996, Bobby won the season-ending race at Atlanta, the same race where his brother Terry won the championship. The two took a victory lap together in what Bobby said was one of the most emotional and memorable moments of his life. That year, he finished 11th in points.
In 1997, Gibbs switched car makes to a Pontiac Grand Prix. Labonte would go on to win the season ending race at Atlanta for the second year in a row. He ended up in 7th place in the standings, his best finish at that point in his career.
In 1998, Labonte won the pole for the Daytona 500, where he eventually finished 2nd to Dale Earnhardt in Earnhardt's only Daytona 500 win. He would later win at Daytona's sister track, Talledega, in the spring, as well as at Atlanta, and also won the pole for the Pepsi 400 at Daytona in summer. He finished the year in 6th in final points, improving by a position.
In 1999, Labonte won five Winston Cup races, the most he has ever won in a single season. He won at Dover in the spring, swept both Pocono races (he was the third to accomplish this particular sweep, after Bobby Allison in 1982 and Tim Richmond in 1986; since 1999, Jimmie Johnson in 2004 and Denny Hamlin in 2006 have also done this), the second Michigan race and the season finale at Atlanta. However, during the season, he suffered a broken shoulder in an accident while qualifying for a Busch Series race at Darlington Raceway, but raced in the Cup event two days later. Labonte started the race, but at the first caution was relieved by Matt Kenseth. He finished second in the points to Dale Jarrett, losing the championship by 201 points.
In 2000, Labonte won 4 races - the second race of the season at Rockingham, the Brickyard 400 at Indianapolis, the Southern 500 at Darlington and the fall race at Charlotte. He led the point standings for 25 weeks straight after taking over at California, and never relinquished it. Bobby would go on to win his first ever Winston Cup championship, finishing ahead of Dale Earnhardt by 265 points.
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