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Bailey emigrated to Canada at age 13 and played basketball until he began interesting himself to track and field in 1991. He, however, did not take tracks seriously before 1994. Bailey set a World Record in 1996 in Atlanta when he finished the race in 9.84 seconds +0.7 m/s wind in the 100 m, beating the previously established record of Leroy Burrell. That win reestablished the image of Canadian athletes, an image Ben Johnson had seriously tarnished in the 1988 Summer Olympics in Seoul after he was tested positive and disqualified after winning the gold medal in the 100 m sprint.
Bailey won two Olympic gold medals, both at the 1996 Summer Olympics in Atlanta, Georgia; the first was in the 100 m sprint, the second in the 4 x 100 m relay. He also won three World Championship ones, as well as one silver. He retired from competition in 2001, after being unsuccesful in the 2000 Summer Olympics due to a pneumonia.