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Once, at the 1936 Games in Garmisch-Partenkirchen.
The first ever Olympic winner, according to tradition, was Coerobus in 776BC. In 1896, the first modern Olympic games, the winners received a silver medal. The gold medal wasn't used until the 1904 summer olympics. There were 91 events, so 91 gold medalists - a list of the winners can be found in the related links.
Early research shows that 11 Canadians won Gold medals in 1936 Olympics.
G.B. won 4 gold at the 1936 Berlin summer Olympics
Jesse Owens won 4 Gold medals at the Berlin Olympics of 1936 (XI Olympiad). However, one was the 4 x 100 meters team relay, which he won with 3 other US runners. *The first Olympic medal won by an African American was a bronze medal in the 400 meter hurdles by George Coleman Poage in the 1904 Olympics.