During the 1980s, Gordon and his family had to overcome an insurance hurdle. The minimum age for driving the sprint cars was 16, and his persistence paid off with an all Florida speed weeks. Supporting his career choice, Gordon's family moved from Vallejo to Pittsboro, Indiana, where there were more opportunities for younger racers. Before the age of 18, Gordon had already won three short-track races and was awarded USAC Midget Car Racing Rookie of the Year in 1989. That season was highlighted by winning Night Before the 500 midget car race on the day before the Indianapolis 500. During the decade, Gordon also ran sprint cars in Australia and New Zealand. In 1990, Gordon won his second consecutive Night Before the 500, the Hut Hundred, and the Belleville Midget Nationals on his way to winning the USAC national Midget title. In 1991, Gordon captured the USAC Silver Crown, and at the age of 20 became the youngest driver to win the season championship. He also won the 4 Crown Nationals midget car race that season. In his midget car career between 1989 and 1992, he finished in the Top 3 in 22 of 40 USAC midget car events. In 1992, Gordon competed in the Slim Jim All Pro Series' Winchester 400, but finished 24th after crashing on lap 172. The following year, he ran a Featherlite Southwest Tour race at Sears Point Raceway, finishing 29th after suffering an engine failure.