Four NHL teams under most pressure to win the Stanley Cup this season

Every NHL team has some level of expectation going into a new season, whether it be to compete for a Stanley Cup, simply make the playoffs or just look for individual progress as part of a rebuild. Each level of expectation brings its own level of pressure.

That is especially true for the teams that are expected to compete for the Stanley Cup. Nobody is going to feel that more than the teams that have failed to make deep playoff runs in recent years, or might be running out of time with their current core group of players. 

So let's take a look at four NHL teams that are going to be facing the most pressure to win during the 2026-27 season.

Edmonton Oilers

There might not be a team under more pressure to deliver than the Oilers.

Connor McDavid is entering year 12 of his career, while having just two years remaining on his contract. He has done pretty much everything there is for an NHL player to do except get his name on the Cup. Every year he goes without it, the emphasis that gets placed on that reality will get louder and louder.

He has to win at some point.

They have to win.

The more he goes without winning there, the more you have to wonder if and when he tries to bail. 

What adds to the pressure this season is that the Oilers have made themselves a focal point for criticism due to the hiring of controversial head coach Mike Babcock. Nobody outside of Edmonton can understand what they see in this attempt, and if it fails, the vultures are going to be out, and nobody in the organization is going to be spared.

Dallas Stars

After reaching three consecutive Western Conference Finals, the Stars took a big step backward in 2025-26, losing in the first round.

Injuries played a big role in that, but that was supposed to be a championship-contending season, and they didn't even get through to the second round. 

The issue the Stars have is that their best player, Jason Robertson, is only signed to a one-year contract and is eligible for unrestricted free agency and a major payday this offseason. If he were going to stay there long-term, he would have likely signed a longer team deal to make that happen.

His lame-duck status really makes this a win-at-all costs type of year. They will still be a good team without him, but he makes them substantially better.

Minnesota Wild

The Wild's situation is very similar to Dallas in the sense they have a superstar player with one year left on his contract, and it's a player everybody knows is probably not re-signing there.

In the Wild's case, it's defenseman Quinn Hughes.

What makes Minnesota's pressure to win is that it paid a steep price to acquire Hughes during the 2025-26 season in an effort to give the team another superstar to pair with forward Kirill Kaprizov. The thinking was that top-10 forward and a Norris Trophy-level defenseman could be the foundation of a Stanley Cup-winning team.

There was also the belief (potentially delusional) that they could convince Hughes to stay.

But all signs point to Hughes wanting to join his brothers (Jack Hughes and Luke Hughes) with the New Jersey Devils as soon as he is free agent-eligible. 

Could they trade him this season, even as a contender? Possibly.

But if they do not, and if they decide to go all-in, this might be one of their best chances for a while. 

Tampa Bay Lightning

The difference between Tampa Bay and the other three teams on this list is they have actually won two Stanley Cups within the past decade. So it's not quite the same pressure.

But there should still be pressure here given the way the past few years have gone.

The Lightning have lost in the first round of the playoffs four years in a row, while their best player, forward Nikita Kucherov, is in the final year of his contract.

There is also the reality that he, and a lot of the Lightning core group of players, are getting deeper into their 30s. This group may not have many more great runs together, and their window might be starting to inch closed. Especially if Kucherov does not re-sign.