San Jose Sharks, 1991, 24 Seasons
This team could lower this list to 11 teams in just a couple of weeks. They are currently matched up with the Pittsburgh Penguins in the Stanley Cup Finals after defeating the Los Angeles Kings, Nashville Predators and St. Louis Blues in the Playoffs.
The San Jose Sharks have been one of the most successful teams to not have won a cup. In their 23 seasons, they have only missed the Playoffs six times and two of those were their first years in the league. That being said, this is their very first trip to the Finals so they have been frustrated as well.
If they don’t win this year, it will get tougher as their big core of Joe Pavelski, Joe Thornton, and Patrick Marleau is all over 30 as well as Brent Burns, Joel Ward, and others on the team. Their window is closing rapidly if they can’t get past the Penguins.
Next: #5, Another Combo Team