He was the first Canadian to legally break the 10-second barrier in the 100 m. Particularly noted for his top speed, Bailey ran 12.10 m/s (43.6 km/h; 27.1 mph) in his 1996 Olympic title run, the fastest ever recorded by a human at the time.

[3] He was inducted into Canada's Sports Hall of Fame in 2004 as an individual athlete and in 2008 as part of the 1996 Summer Olympics 4x100 relay team.

[2] Donovan was fast when he was a young boy, with his former teacher Claris Lambert recounting that "He showed his athletic skills from grade one.

[6] Bailey immigrated to Canada at age 12 and played basketball before graduating from Queen Elizabeth Park High School in Oakville, Ontario.

On July 27, after a very disrupted start to the race, Bailey won the Olympic 100m title setting a new world record of 9.84 seconds.

[11] At the 1997 World Championships in Athens, Bailey attempted to defend his 100m title, but was beaten by Maurice Greene and was forced to settle for the silver medal in 9.91 seconds.

One of his last meets of the season was at the ISTAF Berlin; after finishing 2nd in the 100m, Bailey ran the first leg of the "Dream Team II" in the 4 × 100 m relay: Carl Lewis' last race of his career.

With Leroy Burrell on the 2nd leg, Frankie Fredericks on the 3rd, and Lewis on the anchor, the team won in 38.24 seconds, a meeting record.

Bailey and the 4 x 100 metre Canadian relay team won a silver medal with a time of 38.23 at the 1998 Goodwill Games in New York, finishing behind the United States.

Bailey ruptured his Achilles tendon while playing basketball during the post season of 1998, which effectively began the end of his athletics career.

Bailey won a silver medal with the Canadian 4 x 100 metre relay team with a time of 38.49 at the 1999 Pan American Games in Winnipeg, finishing behind Brazil.

[12] After racing, Bailey started his own company called DBX Sport Management which helps amateur athletes find a way to promote themselves.

He has been inducted into Canada's Sports Hall of Fame twice: in 2004 as an individual, and in 2008 as part of the 1996 Summer Olympics 4 × 100 relay team.

[20][21][22] In 2018, it was reported that Bailey had provided his entire athlete's trust of $3.75 million to Aird & Berlis lawyer Stuart Bollefer, who invested it in what was determined to be a tax evasion scheme by the Canadian government.