Played basketball before his graduation at Queen Elizabeth Park High School in Oakville, Ontario. He began competing as a 100 m sprinter part-time in 1991, but he did not take up the sport seriously until 1994. At that time, he was also a successful stockbroker.

The following year saw he international breakthrough and meteoric rise to fame. At the 1995 World Track & Field Championships in Gothenburg, Sweden, Bailey won both the 100 metre sprint and the 4 x 100 metre relay titles.

As a precursor to the centennial Olympic's being held in Atlanta; Bailey broke the indoor 50m world record during a competition in Reno Nevada. He was timed at 5.56A seconds. He repeated the "double" at the 1996 Atlanta Olympics, setting a world record of 9.84s +0.7 m/s wind in the 100 m (the previous record was set in July 1994 by American Leroy Burrell at 9.85 seconds). Many Canadians felt his victory restored the image of Canadian athletes, which had been tarnished by Ben Johnson's previous disqualified win at the 1988 Summer Olympics in Seoul. Bailey was the 2nd person to hold all the major titles in the 100 m concurrently (World Champion, Olympic Champion & World Record Holder); Carl Lewis was the first to achieve the "triple crown".