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Never, there was no such team as the Chicago Oilers. The Chicago Blackhawks have won the Stanley Cup five times (1934, 1938, 1961, 2010, and 2013). The Edmonton Oilers have won the Stanley Cup five times as well (1984, 1985, 1987, 1988, and 1990)

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11y ago

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The hawks have lost a total of 7 times in the Stanley Cup final series. The first year they lost was in 1931 when they lost to the Montreal Canadiens. The next time they lost was in 1944 when they lost to the Montreal Canadiens again. In 1962 they lost to the Toronto Maple Leafs. Three years later, in 1965, the Hawks lost to the Montreal Canadiens for a third time. In 1971, the hawks were unable to take down the Montreal Canadiens for the fourth time. Two years late, 1973, the Hawks were defeated by the Montreal Canadiens for the fifth time! The last time they lost was in 1992 when they were deafeated by the Pittsburg Penguins. Lets just say the Hawks are to hot against the Montreal Canadiens in Stanley Cup final games.

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Wiki User

11y ago
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Three (3) times.

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Wiki User

15y ago
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Six times.

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Wiki User

7y ago
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Q: How many time did Chicago win the Stanley cup?
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