More than any of the major North American sports, the Stanley Cup tends to be prone to the upset. Consider the President’s Trophy, created in 1985-86 to recognize the regular season champion of the NHL. Since its inception, just eight winners of the Presidents’ Trophy also went on to capture the Stanley Cup. That’s barely one out of four, a 25.8 per cent success rate. Two teams with losing regular-season records have won the Stanley Cup. That’s never happened once in the history of the Super Bowl, World Series or NBA Finals.
Historical Underdog Stanley Cup Champions
The Edmonton Oilers are back in the playoffs this spring for the first time since 2005-06, when they made an unlikely run to the Stanley Cup final, coming out of the Western Conference as the No. 8 seed and falling to the Carolina Hurricanes in a seven-game Stanley Cup final.
In 1990-91, at 27-39-14 the Minnesota North Stars were actually the 17th-best NHL team but earned the final Western Conference playoff spot and then made a shocking run to the Stanley Cup final before being halted by the Pittsburgh Penguins in six games.
Nine years earlier, the 30-33-17 Vancouver Canucks were champions of the Campbell Conference and earned the right to face the defending champion New York Islanders in the Cup final. It struck midnight for Cinderella, as the Canucks were swept by the migthy Isles.