While he continued to run races in the Busch Series, his main success came driving late-model stock cars. In 1987, Labonte won twelve races at Caraway Speedway, clinching the track championship, in addition to working for Jay Hedgecock. The following season, he competed at Concord Motorsports Park, winning six times, and ran six more Busch races, finishing 16th at Darlington Raceway. The next season, he ran seven races and had his first top-five finish at North Carolina Speedway. He had two more top-tens that year.
Next season, he continued his second-division success by winning the NASCAR Busch Series championship with two wins, 10 top-five and 21 top-10 finishes. He also won his first Busch Series race, at Bristol, then won again at Indianapolis Raceway Park in August.
In addition to his Busch Series schedule, he made two Winston Cup starts in a Bobby Labonte Racing car at Dover International Speedway and Michigan International Speedway, finishing 34th and 38th, respectively.
The following season, 1992, he continued racing in the Busch Series. His season was a successful one, and he ended up winning three races (at Lanier, Hickory, and Martinsville speedways respectively), but lost the Busch championship to Joe Nemechek by three points. That championship finish is, to date, the closest finish in either Sprint Cup, Nationwide, or Craftsman Truck Series history.
In 1993, Labonte was called up by Bill Davis Racing to drive in the Winston Cup Series. He signed a contract to drive the #22 Maxwell House Ford Thunderbird. In his rookie season, he won his first pole at Richmond International Raceway, collected one top-five and two top-tens, and finished 19th in points. He was also second place behind Jeff Gordon for Rookie of the Year honors. He also competed in two Busch Series races, winning a pole and finishing 2nd and 24th respectively. Also, Labonte continued to operate his main Busch Series team, hiring David Green to drive for him. Green finished third in points for Bobby Labonte Racing.
The next season, 1994, Labonte achieved his second major success as a car owner when his Busch Series driver, David Green, won the championship. It was the second championship, and fifth top-five points finish in five years for Bobby Labonte Racing. He also ran in the Busch Series himself, making 12 starts and earning a victory at Michigan in August. In addition to his Busch Series exploits, Bobby continued running full-time in the Winston Cup series for Bill Davis Racing. He collected one top-5 and two top-10s and finished 21st in the standings, just missing out on the top 20 because of Todd Bodine's two-position points standings gain in the final race of the season.
At the end of the season, Labonte departed to drive 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, he 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 Labonte said was one of the most emotional and memorable moments of his life. That year, he finished 11th in points. In 1997 Bobby switched car makes to a Pontiac Grand Prix. Bobby 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 Bobby won the pole for the Daytona 500, where he eventually finished 2nd to Dale Earnhardt in Earnhardt's emotional first Daytona 500 win. Bobby would later win at Daytona's sister track, Talledega, in the spring. Bobby also again won at Atlanta and also won the pole for the Pepsi 400 at Daytona in summer. He finished the year in 6th in the standings, improving by a position. In 1999, Labonte won five Winston Cup races, the most he has ever won in a single season. 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. Bobby started the race, but at the first caution a young Matt Kenseth would take over for him in the race. He finished second in the points to Dale Jarrett, losing the championship by 201 points. In 2000, Bobby went on to win 4 races at Darlington, Charlotte, and Pocono (where he swept both races). He was the first to accomplish this particular sweep, which has been followed by Jimmie Johnson in 2004 and Denny Hamlin in 2006. He led the point standings for 25 weeks 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.
In 2001, Labonte finished 6th in the points standings. He also won twice that year at Atlanta and at Pocono. In 2002 Bobby only had 1 win, which was at Martinsville in the spring. He also drove a 9/11 Tribute car in 2002 with the phrase "Let's Roll" on the hood of this stock car. It was his first career short track win at Martinsville. He went on to finish 16th in the standings, and failed to finish in the top 10 for the first time since 1998. In 2003 Labonte rebounded and finished 8th in the standings while winning 2 races at Atlanta, and at Homestead (leading only the final lap). Also Bobby went on a tear during the spring with 3 straight 2nd-place finishes. In 2004 Bobby didn't win a race for the first time since 1994. Labonte finished 12th in the standings. 2005 saw much of the same. Bobby fell out of the top 20 in points, and only had 4 top-5s, one of which was a dramatic 2nd at Lowes Motor Speedway. He also went on to race some truck series events, which included a win at Martinsville. His win there made him join an elite group of drivers that have won in all 3 divisions at one track. In fact, with his win, he became the first driver to do so. He also ran the 24 Hours of Daytona road race, sharing a car with his brother Terry, Jan Magnussen and Bryan Herta. After the disappointing 2005 season, Bobby asked and was granted to be released from Joe Gibbs Racing, having spent the last eleven seasons there. Bobby joined the Petty Enterprises to drive the famous #43.
Bobby won the Busch Series race at Talladega Speedway in April 2007, edging Tony Stewart to the line in a thrilling finish. This was his first Busch Series win since 1998. Bobby would end the year with no top-fives and only three top-ten finishes, but due to a more consistent season, he finished in 18th place in the standings, a three-position improvement over 2006.
In the off season following the 2007 season, Labonte agreed to a 15 race contract to drive the # 21 chevrolet for Richard Childress Racing in the NASCAR Nationwide Series for 2008. RCR's No. 21 team earned six victories in 2007 with driver Kevin Harvick, and has earned two of the organization's four series championships.
In November of 2007, Labonte formed a full-service marketing agency, Breaking Limits
|Year||Races||Wins||Poles||Top 5||Top 10||DNF||Finish||Start||Winnings||Season Rank||Team(s)|
|1993||30||0||1||0||6||6||19.1||20.8||$353,575||19th||Bill Davis Racing|
|1994||31||0||0||1||2||7||21.9||19.9||$512,005||21st||Bill Davis Racing|
|1995||31||3||2||7||14||6||16.3||13.9||$1,219,925||10th||Joe Gibbs Racing|
|1996||31||1||4||5||14||5||17.4||11.8||$1,348,965||11th||Joe Gibbs Racing|
|1997||32||1||3||9||18||1||13.7||13.3||$1,924,250||7th||Joe Gibbs Racing|
|1998||33||2||3||11||18||6||14.2||12.6||$2,620,520||6th||Joe Gibbs Racing|
|1999||34||5||5||23||26||1||9.0||9.5||$3,570,272||2nd||Joe Gibbs Racing|
|2000||34||4||3||19||24||0||7.4||11.6||$4,023,325||1st||Joe Gibbs Racing|
|2001||36||2||1||9||20||6||14.1||17.8||$4,135,851||6th||Joe Gibbs Racing|
|2002||36||1||0||5||7||4||19.8||19.7||$3,851,773||16th||Joe Gibbs Racing|
|2003||36||2||4||12||17||5||16.1||11.9||$4,745,258||8th||Joe Gibbs Racing|
|2004||36||0||1||5||11||2||15.8||16.8||$4,570,545||12th||Joe Gibbs Racing|
|2005||36||0||0||4||7||10||22.7||22.1||$4,627,404||24th||Joe Gibbs Racing|