2

For example, the Stars and the Caps for this year.

Edit:

This is modern era, where we've had full 4-tier playoffs.

  • 4
    Did you want to write "two top teams" instead of "to two teams"? – Martin Apr 23 '16 at 0:27
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    You should also clarify in your question whether you mean Stanley Cup finals or Stanley Cup playoffs. – Martin Apr 23 '16 at 0:48
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    What about Montreal - Calgary in 1988-89 season? And Edmonton-Philadelphia in 1986-87 season? Wikipedia has list of President Trophy winners and their playoff results - you can check there which team they played in the playoffs. – Martin Apr 23 '16 at 0:48
  • Edited for clarity. – gregsdennis Apr 24 '16 at 19:54
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    Please define more specifically when "the modern era" starts; also do you mean the top two teams league-wide (which might be in the same conference, who could obviously never meet in the Finals) or the top team from each conference? – Philip Kendall Apr 24 '16 at 20:23
1

Yes. The NHL spent 25 years with only six teams (the "Original Six" era), and to some extent only three of those teams were competitive, so this has happened many times.

Going even further back (to the 1920s), the playoffs were just a matchup between the top two teams, so this was guaranteed to happen.

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