Never. The Oilers are a hockey team and the Grey Cup is the championship trophy for professional Canadian Football.
The Oilers never reached the Superbowl.
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The Edmonton Oilers have won the Stanley Cup 5 times (1984, 1985, 1987, 1988, 1990).
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The Edmonton Oilers have been to the NHL playoffs 20 times. They also made it to the WHA playoffs 5 times. (This includes preliminary rounds).
Kate and Sawyer have gotten it on 3 times....:)
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None. They stunk
That never happened.