Ottawa Senators, 1992, 23 Seasons
This is actually the second go-round for the Ottawa Senators. The original Senators won the Stanley Cup 11 times back in the early 1900’s. They lost their NHL franchise in the 1930’s but gained a new team in 1992-93.
After missing the playoffs their first four seasons, the Senators went on a run of making them 15 of 19 seasons. This was capped by their Stanley Cup Final in 2006-07 where they lost to the Anaheim Ducks. The Nashville Predators Mike Fisher played on that team.
In 2015-16, the Senators were the top Canadian team point-wise in the NHL. None of the seven teams made the playoffs, however. Like many of the others, Ottawa is currently in a rebuilding mode but are closer than most of the others.
They still feel at least a couple of years away from leaving this list.
Next: #6, The Best Chance