In 1988, Raines competed in five ASA races, and then returned for his rookie year in 1989. In 1990, Raines moved to NASCAR's All Pro Series, where he won Rookie of the Year and finished fourth in the final standings.
He returned to ASA in 1991 for a four-year stint as driver of a new team formed by Ernie Roselli. In 1995, he had moved to join crew chief Howie Lettow and Baker Motorsports. That in turn led to the 1996 championship and Raines' first major NASCAR ride.
Raines entered the 1997 season with a full-time ride, running for Rookie of the Year honors in the #19 PennzoilFord F-150 for Kurt Roehrig. After failing to qualify for the first race of the season, Raines came back to win the seventh race of the season at I-70 Speedway. He finished 15th in points and ended the season with two top-5 and seven top-10 finishes, as well as two outside-pole positions.
In 1998, he won three races (I-70, Louisville and Texas) and earned 6 additional top-5 with fifteen top-tens, ending the season fifth in the standings.
After moving to the Busch and Winston/Nextel Cup series, he has made a total of two starts in the Craftsman Truck Series. In 1999, he made one start in the Truck Series at The Milwaukee Mile for Gerry Gunderman in the #68 truck in 1999 when Raines started 22nd and finished 19th. In 2004, he returned to the series for one race at Atlanta, finishing seventeenth in the #08 1-800-4-A-Phone Chevrolet Silverado for Green Light Racing.
In 1999, Roehrig lost the Pennzoil sponsorship, causing Raines to move up to the Busch Series, signing with the #74 BACE Motorsports team. Raines raced 31 times during the season, with the exception of the Coca-Cola 300, in which Steve Grissom drove. Despite not having major sponsorship, Raines had a best finish of fourth and finished 12th in points, capturing the Rookie of the Year honors.
In 2000, Raines moved to BACE's #33 Bayer Chevrolet Monte Carlo full-time. He had a career-best second-place finish at South Boston Speedway, but with no other top-tens, he fell to fifteenth in the final standings.
He would return in 2001 with Alka-Seltzer sharing sponsorship duties, winning his first career pole at Nazareth Speedway and had a career-high thirteen top-ten finishes, finishing sixth in points. He followed that up with five top-fives in 2002, but fell six spots in points.
In 2003, Raines continued to drive the #33 Outdoor Channel Chevrolet Monte Carlo part-time for BACE while driving full-time in the Cup Series. He had a total of five top-10s in 2003 and finished 39th in the points.
Due to a lack of sponsorship in 2004, BACE closed its Cup team and focused back on the Busch Series. BACE hired Damon Lusk to drive its #74 Outdoor Channel Chevrolet Monte Carlo; but after four races, Raines returned to the team in favor of Lusk, and finished sixth in his first race at Bristol. He ran fifteen races for BACE that season, and drove additional races for Phoenix Racing, Haas CNC Racing, and Kevin Harvick Incorporated.
In addition to his Cup ride in 2005 and 2007, Raines drove part-time for Kevin Harvick Incorporated in the #33 Camping World/Roadloans.com Chevrolet Monte Carlo.
Raines made his Nextel Cup debut with BACE Motorspots at Dover in the 2002 NASCAR Winston Cup Series, finishing 31st in the #73 car. He ran six more races that season in the Winston Cup, driving the #74 Staff America Chevrolet Monte Carlo and his best finish was 29th at Atlanta.
BACE and Raines moved to the Winston Cup full-time in 2003, completing the whole season for NASCAR Rookie of the Year honors. Despite running without major sponsorship, Raines had a sixth-place finish at North Carolina Speedway and finished 33rd in the championship standings, and third in the Rookie of the Year race. Raines had another second-place finish and three consecutive eighth-place runs, allowing him to finish 39th in points despite an abbreviated schedule.
He was expected to complete the full 2007 schedule with Hall of Fame Racing, but was replaced on road course events by Ron Fellows. His best finish in 2007 was ninth at Talladega. At the end of the 2007 season, Tony Raines was replaced by J. J. Yeley in the #96 car for the 2008 NASCAR Sprint Cup Series.