Boston Bruins (2013)
The Bruins suffered the most soul-crushing defeat in their history in the 2013 Stanley Cup. They were cruising against the Chicago Blackhawks before a late meltdown. Boston thought that they had wrapped up their second title in three years but it wasn’t to be (via Boston.com).
Chicago scored two late goals to stun the Bruins and leave the NHL in shock. Their fans wish they could forget that final two minutes at TD Garden but they never will. Unsurprisingly, everybody outside of Boston thought that this was hilarious. Meanwhile, Bruins fans went home with broken hearts.