Now, there are conflicting reports about the validity of this next story, but the rumors alone are enough to make this list.
After the Stars won the Cup in 1999, there was a huge pool party at Craig Ludwig's house. Well, apparently, Guy Carbonneau decided that tossing the Stanley Cup off of the deck of the house and into the pool would be a fun time for all involved.
Due to some bad luck, the Cup didn't reach the pool. Instead, it hit the lip of the pool and suffered serious damage. No league source has confirmed this incident, but how else does a dent like that get there?
