Little began racing on the short tracks of Washington state in the mid-1980s, progressing through the American Speed Association West late model series, the NASCAR Northwest Tour Series, and the NASCAR Winston West Series. In 1986, one year before winning the NASCAR Winston West Series championship, he was named the series' Rookie of the Year. He made his NASCAR Winston Cup debut that same year at Riverside International Raceway, driving a Ford owned by George Jefferson.
Little attempted a full Winston Cup season in 1988 under Junie Donlavey, but posted a best finish of only eighteenth and was released during the year. In 1990, he and his father Chuck fielded their own entry and ran eighteen races with a 33rd-place points finish.
In 1993, Little partnered with Greg Pollex and former NFL quarterback Mark Rypien to form Mark Rypien Motorsports, running a No. 23 Ford on a limited schedule and posting a second-place finish at Dover International Speedway. The team went full-time in 1994 and Little recorded ten top-five finishes, finishing third in the Busch Series points standings.
His best Busch Series season came in 1995, when he won six races — including the first two of the year at Daytona and Rockingham — and finished second in the championship behind Johnny Benson. His other wins that year came at Loudon, Charlotte, Talladega, and South Boston Speedway.
Little's most prominent Winston Cup opportunity arrived when Jack Roush purchased Pollex's No. 97 operation late in 1997. Running full-time for Roush in 1998 with crew chief Jeff Hammond, Little qualified for 32 of 33 races and posted seven top-ten finishes, including a second-place run at Texas Motor Speedway behind Mark Martin. He finished 15th in the final points standings — his career best in the series.
Little was unable to sustain that level in 1999 and 2000, posting five and one top-tens respectively. Late in the 2000 season, Roush replaced him with Kurt Busch, who retained Hammond as crew chief. Little accumulated 217 Winston Cup starts over his career.
In 2001, Little drove the No. 74 for BACE Motorsports in the Busch Series, recording six top-tens and finishing ninth in points. BACE closed early in 2002, effectively ending his competitive career. His final Cup start came at Dover that year.
After stepping away from driving, Little worked as a studio analyst for Speed Channel and provided competition support for the NASCAR Mexico Corona Series. He became tour director for the Whelen Modified Tour before taking on the role of Camping World Truck Series managing director beginning in 2013. In February 2015, NASCAR moved him into a new role as managing director of technical inspection and officiating, where he oversees the sanctioning body's competition integrity from the research and development center in Concord, North Carolina. He is the father of NASCAR driver Jesse Little.