Doest it ever happen in playoff?

[alko]

... that the last winner of Stanley Cup (like Boston Bruis) and the Presidents Trophy winner in actual season (like Canucks) ended in 1. round?
And it could happen, that also the second best team (Rangers) will be done...

Any season, where this occurred?

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[Czech Your Math]

In 2006, TB ('04 Cup) and Detroit (Prez) both lost in round one.

In '71, Boston was both and lost in first round.

 

[Al Bundy*]

We have had a few close calls:

In 1992, President's Trophy winners NY Rangers and defending Stanley Cup champ Pittsburgh were both in do-or-die game 7's- both won.

In 1991, President's Trophy Chicago winner lost in round 1 and defending Stanley Cup champion almost choked a 3-1 series lead to Calgary before Esa Tikkanen's hat trick saved the day.

In 1990, defending Cup champ Calgary lost in round 1 and President's Trophy winner Boston was forced to a seventh game.

In 1989, defending Cup champ Edmonton blew a 3-1 series lead and President's Trophy winner Calgary was extended to game 7 overtime by Vancouver.