Their worst loss, or losses, came at the hands of the Mighty Ducks of Anaheim in the first round of the Stanley Cup playoffs in 2003. The Red Wings were the defending Stanley Cup champions. The Ducks were the #7 seed. The hockey community expected the Red Wings to easily defeat the Mighty Ducks, and move on to the second round of the playoffs. No one predicted what was about to happen! The Mighty Ducks of Anaheim swept the Red Wings in four games and went on to play against the New Jersey Devils in the Stanley Cup finals. The Red Wings were left to ponder not only the fact that they lost in the first round, but how they could be swept by the #7 seed.
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1942 Stanley Cup finals against Toronto Maple Leafs. Wings were up 3 games to none in this best-of-seven series and lost the next four games. It was the first Stanley Cup finals to go seven games, if I'm not mistaken.