Most consecutive first round playoff exits?

[dalewood12]

With the Capitals and Penguins both having three consecutive first-round exists, I was curious about what team post-expansion holds the record. Thanks!

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[Primary Assist]

With the Capitals and Penguins both having three consecutive first-round exists, I was curious about what team post-expansion holds the record. Thanks!

The Leafs unfortunately tie the Caps and Pens here, losing to Washington in 2017 and then to Boston in 2018 and 2019.

I think the "winners" of this thread though are Buffalo, who lost in the 1st round 5 times in a row between 1988 and 1992, and Calgary, who also lost in the 1st round 5 times in a row between 1976 and 1980.

 

[Brodeur]

Not exactly what the OP was asking for, but I randomly felt happy for Teppo Numminen in 2006. He started in the NHL in 1988 and didn't get out of the first round until 2006 with Buffalo. Winnipeg/Phoenix had five consecutive first round exits (1996-2000) during Numminen's time there.

 

[Mightygoose]

Though aided by a weak division, the Hartford Whalers went out in the first round 6 consecutive seasons. 1987 through 1992