Canadian hockey fans have the same conversation every offseason. Will this finally be the year that one of their teams lifts the Stanley Cup again? It has now been 32 years since the Montreal Canadiens last took Lord Stanley’s jug back over the border, and the honest truth is that, for most of that time, it hasn’t really looked like returning.
Even though some of the best players in the league come from Canada – and actually play for Canadian teams – the NHL has been dominated by US teams, increasingly from the south, where the locals are not even used to seeing ice or snow outside of a hockey rink.
With the new season underway and all the top NHL sportsbooks looking at American teams to continue the trend of the last few decades, we thought we would rank the Canadian teams’ chances of ending the Stanley Cup drought.
Calgary Flames
When people say that there is no point in looking at the standings in October, it doesn’t necessarily mean that they are completely wrong about how everything will end up in April. The Flames have missed out on the postseason in four of the last five years, and there seems to be little chance that they will buck that trend this season.
Calgary is towards the bottom of the standings and NHL power rankings right now – and that is more than likely how it will stay for the rest of the campaign. There may be some gradual improvement but the title drought will last a little bit longer yet for the Flames.
Ottawa Senators
Ending a seven-year postseason drought was something to be applauded for the Senators last year, but there is still a very young core to this team that probably doesn’t have what it takes to make it to championship-winning status. This season hasn’t started very well, but little can be read into the first few weeks of action.
Admittedly, there is expectation, rather than hope, now for Ottawa to make the playoffs, but few actually believe the Senators will do anything of note once they make it that far. There are still too many better teams to get past before Canada is forced to get behind this team at the Stanley Cup finals.
Vancouver Canucks
Canucks fans will be hoping that last year was merely a blip in their team’s return to contention. The narrow second-round loss to the Oilers the year before promised much, but that potential was ultimately wasted as Vancouver failed miserably.
The new season has started brightly, if unspectacularly, but Thatcher Demko is looking good tending goal. There is little chance of Vancouver returning to the Stanley Cup finals for the first time since 2011, but the playoffs should not be just a wild dream.
Winnipeg Jets
How well Jonathan Toews returns to the NHL after two years away was the biggest question facing the Jets this season, and the jury is obviously still out. Winning the Central and the Western Conference last year didn’t seem to alter anyone’s views of the Jets as championship contenders either.
In all likelihood, it will be more of the same for Winnipeg. It will do well in its division and conference before falling short against one of the bigger teams in the playoffs. It doesn’t feel like the Jets will be the team to end Canada’s absence of Stanley Cup success.
Montreal Canadiens
For many neutrals (as far as you can be neutral with NHL hockey, that is) it should be Montreal who finally wins another Stanley Cup for Canada. The Habs are the most successful team of all time, of course, and were the last ones from north of the border to lift the famous trophy.
Last season saw the end of Montreal’s postseason drought as well, so there were high hopes of improvement going into 2025-26. Cole Caulfield is developing into a more all-round player than some people expected, and the Canadiens will be keen to prove last year was not just a fluke.
Toronto Maple Leafs
A lot was said in the offseason about Toronto struggling to replace what Mitch Marner brought to the team. His move to Las Vegas obviously hit the Leafs’ chances of claiming their first Stanley Cup triumph since 1967, but the new season has started brightly.
There will always be the danger of what comes up in the postseason for Toronto, but a good regular season, once again, can mitigate that. William Nylander has shown there is life after Marner and that should give all Leafs fans hope for the season ahead.
Edmonton Oilers
No one wins a Stanley Cup in October, so the less-than-exemplary start to the new season should not overly concern Oilers fans. Connor McDavid may not have begun his own personal campaign in scintillating fashion. But the fact is that he is arguably the best player in the NHL – and has the MVP awards to back up his claim.
Although Toronto and Winnipeg, in particular, would probably argue the point, the Oilers seem to be Canada’s best chance of Stanley Cup success while McDavid is still playing for the Oilers. The regular season has a long way to go – and the loss in the finals last year should be an added incentive for Edmonton this time around.
