The Bruins have enjoyed some high points in the Stanley Cup Playoffs, of course.

This year is the 50th anniversary of the Bobby Orr Stanley Cup team in 1970 when he went flying through the air to immortality. That’s a cherished memory.

And the Bruins Cup team from 2011 is approaching a 10-year anniversary next season after giving everybody something to talk about when they got together for a team-wide video stream watching a replay of Game 7 against Vancouver a couple of weeks ago.

Get the latest news and analysis on all of your teams from NBC Sports Boston by downloading the My Teams App

But there have been more heartbreaks and disappointments when it comes to the Bruins and playoff history. And most of them have come at the hands of the Montreal Canadiens in the 1970s, 1980s and even within the last 10 years.

There is also, of course, the new heartbreak that tops the list after the Bruins couldn’t close the deal on home ice in Game 7 against the St. Louis Blues with everything on the line.

Here are the Top 10 heartbreaking moments from Bruins playoff history with way, way, way too many of them coming against the Bleu, Blanc et Rouge.


Click here for the gallery.