Stanley Cup Or Bust: Which Canadian Team Will End Drought?

Stanley Cup Or Bust: Which Canadian Team Will End Drought?
By Steve Bittenbender
Fact Checked by Thomas Leary

We’ve now officially reached 30 years since the last Canadian-based team hoisted Lord Stanley’s Cup at the end of the NHL season. It’s a record of futility that leaves many hockey fans on both sides of the border dumbfounded.

To be honest,, your top source for Ontario sports betting, was ready to write this column more than a week ago after the Florida Panthers took a 3-0 lead on the Edmonton Oilers. You know the rest of the story. The Oilers roared back to win three straight and force a Game 7, only to see the Panthers avoid ignominy by pulling out a 2-1 victory Monday to win their first Stanley Cup Final.

Canadian teams have reached the Stanley Cup Final seven times in the years since the Montreal Canadiens won it in 1993. In those seven series, five of them have gone seven games, but none were as gut-wrenching as this year’s edition.

The Great Canadian Drought is nowhere near other streaks of misery. The Boston Red Sox went 86 years between World Series titles. The Chicago White Sox needed 88 years to win their next title, and their neighbors to the north, the Chicago Cubs, endured 108 years of futility before finally ending their skid. A Canadian team could win it next year, or in 2034, or in 2044. It can’t last that long, right? Right? created these hypothetical odds for which Canadian NHL franchise will win a Stanley Cup next; these odds are not at any Ontario sportsbook apps operator.

Jim Tomlin contributed to an earlier version of this story.

Next Canadian NHL Franchise To Win A Stanley Cup Odds


Percentage Chance


Edmonton Oilers



Toronto Maple Leafs 



Vancouver Canucks 



Winnipeg Jets



Montreal Canadians



Calgary Flames 



Ottawa Senators



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Can The Oilers Strike Next Season?

The Edmonton Oilers came this close to ending the streak this year. Unfortunately, Florida’s defense was just too much for the Oilers to overcome. The Panthers played Game 7 as they did for most of the first three games.

If you look at the futures boards at most sportsbooks, you’ll see the Oilers either as the favorite to win next season or as one of the top teams to compete for the Cup. At NorthStar Bets Ontario Sportsbook, the Oilers are available at +1000, with only the Panthers, Colorado Avalanche and Dallas Stars priced lower at +900.

However, it’s fair to question just how long the Oilers window will stay open. Connor McDavid and Leon Draisaitl are great players, but Draisaitl will be an unrestricted free agent after next season and McDavid will be a UFA the year after that. Edmonton will be hard-pressed to keep both and retain enough salary cap room to field a competitive team. 

Will Toronto Break Its Own Streak?

The Toronto Maple Leafs are the Boston Red Sox or Chicago Cubs of Canada. It’s been 57 years since the Leafs have even been in a Stanley Cup Final. Management has made moves in recent years to significantly upgrade the team, but they have not been able to get to a conference final since 2002.

Similar to the Oilers, the window may be closing soon on Toronto. There are reports already that Mitch Marner, third in points this past season with 85, has been dealt to Utah. Both Tyler Bertuzzi and Max Domi are unrestricted free agents. If Joseph Woll, who is a restricted free agent after next season, can secure the top goalie position, then the Leafs will be able to move some money around and shore up the team elsewhere.

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Vancouver, Winnipeg Could Surprise

The Vancouver Canucks were a pleasant surprise in 2023-24, winning the Pacific Division. While they were eliminated by the Oilers in the second round of the playoffs, there is hope they’ll be able to build upon the momentum created this season. The core of that team should be back in Vancouver this fall, but the Canucks have a tough division that includes the Oilers and Vegas Golden Knights. Don’t expect them to sneak up on people in 2025.

At bet365 Ontario Sportsbook, the Canucks have odds of +1500 to be the champions next season.

Defense comes first for Winnipeg right now. The Jets allowed a league-low 199 goals this past season, and it certainly helps to have Connor Hellebuyck, a two-time all-star goalie and former Vezina and Jennings trophy winner, between the pipes. As long as he can maintain his top form, the Jets should be considered no worse than a dark horse Stanley Cup contender. Oddsmakers at BetMGM Ontario Sportsbook have priced the Jets at +2200 on their futures board for next season.

Fans In Montreal, Calgary and Ottawa May Have To Wait

It’s been downhill for the Montreal Canadiens since their surprise run to the 2021 Cup Final. They’ve not only missed the playoffs in each of the last three seasons, but they’ve also finished last in the Atlantic Division. Expectations will be higher for Martin St. Louis’ team heading into 2024-25, and there’s apparently some young talent in the Canadiens farm system. A return to the team’s glory days is not a realistic expectation for next season, but leaving the basement of the Atlantic should be a reasonable expectation. 

This is a team that’s probably a few years away from being serious contenders.

For those more hopeful Habs fans, Sports Interaction Ontario Sportsbook has the Canadiens Cup odds set at +15000 for next season.

The Calgary Flames were in a not-so-good middle ground this past season. Not really good enough to contend for the playoffs, yet not bad enough to be in position for a high draft pick. There’s about $23.2 million in salary cap space this offseason, and the team appears to be building for the future after trading goaling Jakob Markstrom to the New Jersey Devils last week. They’ll get the Devils first-round pick next season, so the potential is there for two top-half first-round picks in the 2025 draft. The Flames also received Kevin Bahl, a 6-6 defenceman who turns 24 on Thursday. He could help the Flames cut down on the 271 goals they allowed last season.

DraftKings Ontario Sportsbook is offering the Flames at +7500 for next season.

Our odds might be unfairly low for the Ottawa Senators here. The Sens have missed the playoffs in seven straight seasons. However, they made some waves before Game 7 Monday when they got Vezina Trophy-winning goalie Linus Ullmark from the Boston Bruins for goalie Joonas Korpisalo and center Mark Kastelic and the No. 25 pick in Friday’s NHL Draft.

Some oddsmakers already see the Sens as a team to contend for a playoff spot next season. At BetRivers Ontario Sportsbook, the Senators' 24-25 Cup odds are +3500, the eighth lowest among Eastern Conference teams.



Steve Bittenbender

Steve is an accomplished, award-winning reporter with more than 20 years of experience covering gaming, sports, politics and business. He has written for the Associated Press, Reuters, The Louisville Courier Journal, The Center Square and numerous other publications. Based in Louisville, Ky., Steve has covered the expansion of sports betting in the U.S. and other gaming matters. He shares his expertise on OntarioBets, among other sites.

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