Landry embarked on his career while in his teens, earning his first victory on June 21, 1981, at Fort Erie Racetrack.
[1] In addition to numerous Graded stakes race wins, in 1998 Robert Landry won two of the three Canadian Classics.
In 2003, Landry was voted the Avelino Gomez Memorial Award, an annual honour given to a jockey in recognition of their significant contribution to the sport of Thoroughbred racing.
[2] In addition to volunteer work for various children's charities, Robert Landy has been an active supporter and a member of the board of directors of the LongRun Thoroughbred Retirement Society.
[3] The Rexdale organization is dedicated to providing aged Thoroughbred racers with a permanent adoptive home or alternative careers as pleasure horses or companion animals.