They have won Stanley Cups and boasted some of the greatest players ever, but they have also suffered heartache in the playoffs.
What are the most painful seasons the franchise has endured? What makes a painful season?
For this list, a painful campaign does not necessarily have to be miserable on the whole—it could be a season that resulted in a playoff trip ending in heartbreak.
Here are the five most painful seasons in Boston Bruins history.
The Bruins had a solid year in 1986-87, earning 85 points and securing a playoff berth.
However, the end of the season had a familiar tone: a loss to their archrival.
For the fourth straight season, the Bruins were eliminated in the first round of the playoffs by the Montreal Canadiens. To make things worse, this was the second straight year they were swept out by the Habs.
To not advance past the first round of the playoffs for four straight years and lose to your hated rivals made this a very painful end to the season for Boston.
The Bruins had another great regular season in 2009-10, easily securing a playoff berth and having home ice in the conference semifinals against the Philadelphia Flyers.
But we all know what happened in that series.
The B's blew a 3-0 series lead and three-goal lead in Game 7 to lose the series and any hopes of winning their first Stanley Cup since 1972.
The humiliation and second-guessing that come with a loss like that in the playoffs stay with a franchise for a long time.
Well, unless you win the Cup the very next season.
The 1996-97 season was something that many Bruins fans had never experienced.
For the first time since 1968, the B''s failed to reach the postseason. Not only that, Boston finished in last place in the Northeast Division by only tallying 61 points in 82 games.
Ray Bourque was getting up there in age and his chances of ever winning a Cup in Boston were waning. Three years later, he was dealt to the Colorado Avalanche.
The '97 season was the last one coached by Steve Kasper, as the Bruins brought in the legendary Pat Burns the following year.
Bruins fans hope to never experience anything like 1996-97 ever again.
1961-62 was a disaster for the Bruins, as they finished with the worst record in the league. They managed only 38 points in 70 games, which was 22 points behind fifth-placed Detroit.
Boston scored 177 goals and gave up 306. That's painful.
The Bruins had a record-breaking season in 1970-71, but it was the way it ended that made it so painful.
The B's finished with the best record in the league (57-14-7, 121 points), Phil Esposito scored 76 goals and he and Bobby Orr finished first and second in the scoring race.
But that all came crashing down in the first round against the Montreal Canadiens.
The Habs upset the B's in seven games after coming back from a 3-2 series defecit. When the playoffs began, it was a foregone conclusion that Boston was going to win the Stanley Cup. The Bruins were just too good.
Not even getting out of the first round when defending the Cup makes this the most painful season in Bruins history.