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Dragon began racing in the late 1960s, driving late models and modifieds, winning many championships over the years.[2] Dragon competed in what is now the American Canadian Tour, winning 17 races between 1979 and 1985.[3] Dragon made his NASCAR Busch Grand National Series debut in 1986. He attempted eight races in the No. 71 Buick, making the field in seven of them. He ran seven more races the following year, in addition to running nearly the entire NASCAR Busch Grand National North Series, where he would win a race. Dragon ran a handful of NASCAR Busch Series races between 1988 and 1995, finishing a career high 4th in a race at Oxford Plains Speedway in 1988. He also continued competing in the Busch North series, running races between the late 1980s and 2004, where he competed full time for the first time. Dragon won 14 races in the series, as well as finishing in the top ten 115 times.[4] Dragon was inducted into the New England Auto Racers Hall of Fame in 2009[2] and the Vermont Sports Hall of Fame in 2015.[5] Bobby and his brother Beaver were inducted into the Living Legends of Auto Racing Hall of Fame in 2018.[6]