Which Canadian team is likeliest to break country's 30-year Stanley Cup drought?

A significant chunk of current NHL players weren't even born the last time a Canadian team won the Cup.

There isn't a Canadian team left in the NHL playoffs, which means that the country's Stanley Cup drought is going to go beyond the 30-year mark.

When the Montreal Canadiens hoisted the Cup in 1993, the first Jurassic Park movie was a couple of days away from coming out, and Kim Campbell was about two weeks from become Canada's first female prime minister. Of the 951 players who appeared in the NHL this season, 695 of them hadn't been born yet.

It's an odd drought to wrap your head around because it's no Canadian fans' top priority, and it could end in a way that would be unsatisfactory to most of them. Habs fans aren't interested in seeing the Toronto Maple Leafs or Ottawa Senators crowned champions. The Flames faithful don't want to watch Connor McDavid and Leon Draisaitl lift the trophy in Edmonton.

While a number of Canadians are displeased with the situation to some degree, most of them only want it resolved on their terms. Even so, for a hockey-mad country, the lack of a championship is jarring.

Below is a power ranking of the teams most likely to break the streak and bring Canada an elusive Stanley Cup — and what it would take for each of them to grab the country's first title in a generation.

The NHL playoffs are without a Canadian team, which means fanbases north of the border are left wondering when the country's drought will finally end. (Getty Images)
The NHL playoffs are without a Canadian team, which means fanbases north of the border are left wondering when the country's drought will finally end. (Getty Images)

1. Edmonton Oilers

Upside: As long as you've got Connor McDavid and Leon Draisaitl you've got a chance. That might sound overly simplistic, but it's also true.

Downside: The Oilers have issues keeping the puck out of their net, but they don't have much flexibility to address them. There isn't a horde of blue-chip prospects racing to reinforce this group. They are what they are, and will need to get over the hump with minimal adjustments.

What it will take: This team would have to keep lighting lamps at an elite pace all the way through the playoffs. They've got the horses to do that, and have had more playoff success over the last two seasons than any other Canadian squad.

What Edmonton really needs is some quality goaltending. With a hot goalie there could be no stopping this group.

2. Ottawa Senators

Upside: This team is absolutely packed with quality players 25 years or younger, headlined by Brady Tkachuk and Tim Stützle. The defence corps is solid and locked-in contractually. New ownership is coming and the club projects to have significant cap room in 2023-24 and beyond.

Downside: We haven't seen this group make the playoffs yet, so there's a long way to go. The Senators used seven different goaltenders during the regular season and needs a solution in the crease.

What it will take: This might seem like a stretch, but this team has an incredible ceiling. A few of the young players on this squad are already stars and project to get better and better. The team posted solid underlying numbers, during the season but was thwarted by awful goaltending.

The addition of Jakob Chychrun shows Ottawa sees itself as ready to win. To be clear, the Senators are not the second-best team on this list for 2023-24. But if the Oilers, Maple Leafs, and Flames falter in the near term, Ottawa is Canada's best hope for the future.

3. Toronto Maple Leafs

Upside: Theoretically, this team can still score at an elite level, and its defensive structure has taken a step forward in recent years. Auston Matthews remains an outstanding centrepiece, and he seems interested in making a long-term commitment. Most of this group remains in its physical prime.

Downside: There's plenty of turmoil surrounding this team heading into the offseason and it's unclear who will be back next season. That applies to players, coaches, and decision makers. Breaking up this core is a possibility, but that could easily make this team worse. The prospect pool is simply unimpressive.

What it will take: The magical playoff run this team has never had. If Matthew Knies became a reliable top-six forward, that would help backfill possible free agent departures.

As per usual, though, a Stanley Cup win for the Maple Leafs would mean the top of their roster over-performing rather than going quiet. We don't have any proof of concept for that yet.

4. Calgary Flames

Upside: Firing Darryl Sutter may have reinvigorated this squad. It seems fair to project a better year from Jonathan Huberdeau in 2023-24, and there's plenty of scoring depth behind him. This was one of the best puck-possession teams in the NHL last season despite its uninspiring results.

Downside: It's tough to know what Calgary is going to get from Jakob Markström (or Daniel Vladar) between the pipes. This is a veteran team with plenty of players in their late twenties or early thirties, and more room for internal decline than growth.

What it will take: Whoever is the new coach will need to get this squad firing on all cylinders right out of the gate. This is a win-now operation. Just a year ago, the Flames put together an 111-point season, and it's not outrageous to think they could do something similar again.

The loss of Matthew Tkachuk hurts, but this group has talent. Probably not enough, but more than any team below them on this list.

5. Vancouver Canucks

Upside: Elias Pettersson found a new level in 2022-23 that confirmed his status as an elite player. Quinn Hughes could be a top-notch number one defenceman. Vancouver was an above-average offence in 2022-23, putting them a Thatcher Demko bounce-back away from respectability.

Downside: Depth is an issue, Pettersson needs a long-term deal, and they won't have any cap space to play with until 2024-25. The defence corps outside of Hughes leaves plenty to be desired.

What it will take: Petterson and Hughes will have to be superstars while Andrei Kuzmenko builds on an exceedingly promising rookie season.

If J.T. Miller can avoid any kind of performance decline, that'd also be swell for Vancouver, and a dash of vintage Demko wouldn't hurt. Plenty would need to come together, but the right bargain shopping around the stars could have this team looking competitive in a hurry.

6. Montreal Canadiens

Upside: Cole Caufield is the real deal, and Juraf Slafkovsky is a first-overall pick with plenty of untapped potential. The biggest contributors are all locked in and the defence corps has plenty of young talent.

Downside: This team isn't particularly close to being good now, and for a team with its lack of established top-end talent, its cap flexibility isn't impressive. Goaltending is a black hole at the moment.

What it will take: For Montreal to compete for a Cup, it needs almost all of its young NHLers to take a step forward simultaneously. Teams have certainly grown up together before, but this group is a long way from being a contender.

This is a group on the way up, but it's got a long way to go and with no generational talent to put the team on his back. It's not hard to envision them as a playoff team in the near future, but there's a difference between squeaking in and winning it all.

7. Winnipeg Jets

Upside: There are still some quality players on the roster. Winnipeg was one of just three Canadian teams to make the playoffs this year.

Downside: The current core seems to have run its course, with only Kyle Connor and Josh Morrissey signed long term. Winnipeg traditionally struggles to entice free agents, and the Jets' prospect pool ranks in the middle of the pack.

What it will take: The most likely outcome for the Jets this offseason is some kind of reset wherein the team ships out veterans it feels unable to retain. However, it's possible that the team decides to take one final run behind impending free agents Mark Scheifele, Blake Wheeler, and Connor Hellebuyck.

Hellebuyck can still steal a series — or three — and the NHL playoffs are chaotic enough that the Jets sneaking in next year and winning it all is technically on the table. There's a reason they're ranked seventh on this list, though.