A member of the Royal Canadian Yacht Club, Clifford Howard was winning junior-level races at the age of 10 and acquired four first-place medals with the Junior division of the club during the 1930s (1933, 1935, 1936, and 1939). He served in World War II with the Royal Canadian Naval Volunteer Reserve as a navigator in the North Atlantic with convoy escorts, eventually reaching the rank of Lieutenant. Returning to Canada after the conflict, he reached his competitive racing peak during the 1950s and was a member of the crew that won the 1954 Canada’s Cup International Challenge Match. Two years later he competed for his country in the Three Person Keelboat (Dragon), Mixed sailing event at the 1956 Summer Olympics alongside Dave Howard and Donald Tytler, placing eighth in a field of 16 competing vessels. After the Olympics he maintained a lower profile, but remained a lifelong member of the club.