He also partnered in dirt tracks in Paducah, Kentucky and Macon, Illinois, and acquired the All Star Circuit of Champions (ASCS) winged sprint car series.
After retiring from NASCAR in 2016, he returned to dirt-track competition on a part-time basis. He also competed at the Rolex 24 at Daytona on five occasions. During that period, he became owner of the legendary Eldora Speedway dirt-track Mecca in Ohio, launched USAC and World of Outlaws teams under his Tony Stewart Racing umbrella, as well as the NASCAR team Stewart-Haas Motorsports. He moved to the Cup Series in 1999 and won three championships. A former USAC triple-crown winner, Stewart competed in both the Indy Racing League and the NASCAR Busch series concurrently in the late 1990s, winning an IRL title in 1997. Stewart’s personal involvement in and subsequent business portfolio is perhaps the most extensive in all of motorsports. That announcement - and the former NASCAR champion’s moonlighting behind the wheel of various dragsters in recent months - are quite a turn of events for a man who has openly admitted to denying any interest in pursuing drag racing prior to his romantic relationship with Pruett. On October 14, in a press conference held at the zMax Dragway in Concord, North Carolina with NHRA President Glen Cromwell in attendance, Tony Stewart announced his entrance into professional drag racing with a new team composed of fiancee Leah Pruett and her Funny Car stablemate Matt Hagan.
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