Consecutive losses to eventual Stanley Cup champion

[daver]

The Oilers are currently on a three year streak of losing to the eventual Cup champion in the playoffs.

When do you this last happened?

 

[Crosby2010]

I know the reverse happened before. The 1972-'74 Rangers beat the defending Cup champs three years in a row. The 1989 and 1990 Kings did it two years in a row. Ironically the Kings in those same years also lost to the eventual Cup champs.

I guess the easiest pick for your thread would be the 1977-'79 Bruins who lost to the Canadiens all three times. Actually 4 in a row with losing to the Islanders in 1980.

It actually almost happened for Boston a total of 5 times in a row! 1988-'92. The only year was 1989 when the Habs lost in the Cup final.

Winnipeg 4 out of 5 years (only time not in 1986) against Edmonton.

Rangers did it 4 out of 5 years from 1979 to 1983, only not doing it in 1980.

Three times in a row would have happened plenty in the original 6 days.

 

[kaiser matias]

Canucks did it in 2010, 2011, and 2012.

 

[mrhockey193195]

Not quite what you're asking, but the Rangers lost to either the cup winner or runner up for 5 seasons in a row between 2012-2016 (in no small part to making the ECF themselves three of those five years).