Unfortunately the answer is none in both Montreal in 1976 Summer Games and Calgary in the 1988 Winter Games. They are hoping for much better when they hold the 2010 Winter Games in Vancouver.
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Canada won 14 gold medals at Vancouver in 2010.
As of August 18, Canada has won 251 Summer Olympic Medals (57 gold, 88 silver, 106 bronze) and 119 Winter Olympic medals (38 gold, 38 silver, 43 bronze).
Through the 2008 Games in Beijing, the Canadian athlete that has won the most Olympic medals is speed skater Cindy Klassen who won 6 Winter Olympic medals. Gold - 1) 2006 - 1500 meters Silver - 1) 2006 - 1000 meters, Team pursuit Bronze - 1) 2002 - 3000 meters 2) 2006 - 3000 meters, 5000 meters The Canadian athlete with the most Summer Olympic medals is Phil Edwards who won 5 medals in athletics, all bronze: 1) 1928 - 4x400 meter relay 2) 1932 - 4x400 meter relay, 800 meter run, 1500 meter run 3) 1936 - 800 meter run
Canada won the most gold medals in one Winter Olympics with 14 in 2010.
Gaétan Boucher, a Canadian legend, in my opinion :) He won 2 of his gold medals in a single olympics game (1984 I am 95% sure)