Pittman began racing sprint cars in 1996, initially competing in the American Sprint Car Series before joining the World of Outlaws Sprint Car Series on a full-time basis in 1999. After a difficult start to his 2001 national tour campaign, he made a late-season decision to pursue the World of Outlaws Gumout Racing Series — the circuit's support series — and won that championship.
During the winter of 2002–2003, Pittman raced in Australia and won the World Series Sprintcars championship, becoming the only American driver to win the title. He was also named Australian Sprint Poll Driver of the Year for that season.
After the 2008 season Pittman stepped away from the full World of Outlaws national tour for four years, competing instead in regional series in Pennsylvania. He won the 2010 Keystone Cup Sprint Car Series championship and the 2012 All Star Circuit of Champions Eastern Region title, the latter while racing for Heffner Motorsports.
Pittman's most prominent single-event victory came in 2008 when he drove for Titan Racing USA and won the Kings Royal at Eldora Speedway, beating Jason Meyers and Chad Kemenah.
Returning to the national tour in 2013 with Kasey Kahne Racing, Pittman won the overall championship at the DIRTcar Nationals miniseries at Volusia Speedway Park to open the season. He went on to claim the 2013 World of Outlaws STP Sprint Car Series championship with eight wins across the year, beating Donny Schatz by 14 points at the end of the season. He was the first driver from Oklahoma to win the World of Outlaws championship.
In 2014, Pittman again won the Speed Sport World Challenge at Knoxville Raceway — his third win in that event, following previous victories in 2004 and 2005 — and finished second in the championship. He also won 14 events during the year, including four in succession.
In 2015, Pittman won his second DIRTcar Nationals championship. He remained with Kasey Kahne Racing for 2016, recording eight wins and 45 top-five finishes on his way to a runner-up finish in the championship, accumulating 68 top-ten results.
Pittman left Kasey Kahne Racing after the 2018 season, which had seen him fourth in points with nine wins. He joined Roth Motorsports for 2019. That year he won his third DIRTcar Nationals championship at Volusia, added four World of Outlaws wins, claimed his second Gold Cup at Silver Dollar Speedway, and became the first four-time winner of Oskaloosa Speedway's Front Row Challenge for 360 sprint cars. He finished fourth in championship points.
Pittman returned to Roth Motorsports for 2020. In July he won the World of Outlaws Elimination Showdown special event at Cedar Lake Speedway. He tested positive for COVID-19 in August and missed two events before returning. In September he announced he would step away from full-time competition at the season's end; he also departed Roth Motorsports at that point. His final win with the team came at Lawton Speedway in his home state of Texas, an emotionally significant result. He finished the 2020 season with Heffner Motorsports to complete his farewell campaign, placing seventh in the championship standings.
Pittman resides in Flint, Texas, and owns and operates Ultra Shield Race Products. Since retiring from full-time competition he has continued to make limited appearances; through 2026 he had contested five World of Outlaws races in his semi-retired capacity, recording one top-five and two top-ten finishes.
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