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No the Stanley Cup has never been decided by a shoot-out. It is actually impossible because in the Stanley Cup Playoffs overtime has a different format from the regular season. In the playoffs when a game is tied at the end of regulation (3x20 min periods and score tied) the teams enter sudden death overtime (which means the first team to score wins), but the overtime is very similar to regulation play. The teams skate 5-on-5 like a normal period and the periods are 20 mins long, also like a normal period. The game continues until one team scores. This means that theoretically if no one scored the game would go on forever. The most recent memory that comes to mind is the 1996 Stanley Cup Final where Uwe Krupp of the Colorado Avalanche scored the cup-clinching overtime goal in the third period of overtime (the sixth period of the game).

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Q: Has a Stanley cup championship ever gone to a shootout?
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