Born in Drayton Valley, Alberta, Canada, Boulanger began his career in 1987 at Tampa Bay Downs then went to the Pacific Northwest where he was the leading jockey for three straight years from 1989 through 1991 at Longacres Racetrack in Washington state.
[4] While competing in Florida in the winter of 2005, Gary Boulanger suffered a life-threatening and career-ending injury in a racing accident at Gulfstream Park in the January 30 running of the Mac Diarmida Handicap.
[5] Called "one of South Florida's best riders the past several years" by The New York Times,[6] Boulanger underwent surgery for a ruptured spleen, broken ribs, as well as a detached tendon in his left elbow.
[9] On February 17, 2013, Boulanger returned to the saddle at Tampa Bay Downs, finishing 9th aboard Spring a Latch, a horse in which he is also trainer.
[10] In 2017 he became the 33rd recipient of the Avelino Gomez Memorial Award given to jockeys who have made significant contributions to Canadian Thoroughbred racing.