Most Frequent Stanley Cup Finals Matchups

Source: https://www.sporcle.com/games/PhilThePain/nhl-most-common-stanley-cup-finals, Created on 2/11/2017

The Top Ten

1 Toronto Maple Leafs vs Detroit Red Wings

2 Boston Bruins vs Montreal Canadians

3 Montreal Canadians vs Detroit Red Wings

4 Montreal Canadians vs Toronto Maple Leafs

5 Chicago Blackhawks vs Montreal Canadians

6 Toronto Maple Leafs vs New York Rangers

7 Pittsburgh Penguins vs Detroit Red Wings

8 Boston Bruins vs Edmonton Oilers

9 Montreal Canadians vs Calgary Flames

10 Philadelphia Flyers vs Edmonton Oilers