I was watching Oilers–Stars back in March, and something hit me: Canada hasn’t won a Stanley Cup since 1993. That’s not a typo. The country that gave us Wayne Gretzky, Tim Hortons, and hockey itself hasn’t lifted the Cup in over three decades.
That’s right, thirty-two years since Canada hoisted the Stanley Cup. That feels… impossible. Like hearing Italy hasn’t made good pasta in 30 years.
Canada’s in some weird hockey purgatory. They invented the game, breathe it, live it, bleed it… and yet the Cup keeps packing its bags and flying south every June.
Do any Canadian NHL teams have a shot to break the Stanley Cup drought this year? The answer is yes!
Is this the Year? The Stanley Cup Futures Odds for Canadian Teams (May 14th Update)
Short answer? Maybe. Long answer? The odds are where things get interesting — or painful if you’re north of the border.
The playoffs are knocking and a few Canadian teams are once again lining up to take their shot. But if you’re looking to wager on the Stanley Cup, sportsbooks aren’t exactly betting the farm on them.
Here’s how things look as of April:
| Team | BetUS (Offshore) | MyBookie (Offshore) | BetMGM (U.S.) | Caesars (U.S.) |
|---|---|---|---|---|
| Edmonton Oilers | +300 | +320 | +300 | +305 |
| Toronto Maple Leafs | +950 | +950 | +900 | +1000 |
| Winnipeg Jets | +4000 | +4000 | +5000 | +5000 |
| Ottawa Senators | Knocked Out | Knocked Out | Knocked Out | Knocked Out |
| Montreal Canadiens | Knocked Out | Knocked Out | Knocked Out | Knocked Out |
| Vancouver Canucks | N/A Off the Board | N/A Off the Board | N/A Off the Board | N/A Off the Board |
| Calgary Flames | N/A Off the Board | N/A Off the Board | N/A Off the Board | N/A Off the Board |
Odds last updated on May 14, 2025 at 11:00am EST
Edmonton Oilers: They Are Back as The Favorites Up North
You want a legit Stanley Cup contender from Canada? The Oilers had started there, then slipped out of that spot. Most books had Edmonton between +850 and +950 in April, but put them in the +2200 late in the month.
As of May 14th (the last update to this page), you can find their odds sitting right at around +300. That’s as close as anyone in Canada has come to being the front runner this year.
Connor McDavid and Leon Draisaitl have recovered their beast mode status. They made the Final last year, and they are on track for a repeat now.
If anyone’s gonna end the drought as of today, the Oilers are your best bet. Literally.
Winnipeg Jets: Quiet, and Fading
The Jets are interesting. They improved their odds from around +1000 earlier in April, to +700 to +800 early in the playoffs. Right now in mid-May, they’ve all but fallen out of the race at +4000.
They’re not flashy, but they were consistent, physical, and played with a bit of a chip on their shoulder. Can they hang on, or are they toast?
They’ve never made the Final since moving from Atlanta. But if you’re looking for a dark horse from the Great White North, this is the team to keep an eye on. They are falling pretty far back though.
Toronto Maple Leafs: Big Hopes and Big Shifting Momentums
Toronto was sitting around +1200 early in April, and after the first few playoff games, they have moved down to the +700 range. As of this update, they have moved back to the +900 to +1000 range. That makes this team a top-five contender at most books still, but everyone, calm down… It’s the Leafs.
If you’ve ever met a Leafs fan, you know they’re teetering between hope and heartbreak every spring. That’s because they always look ok on paper, but they haven’t even made the Final since 1967. I wasn’t alive. My dad was barely alive.
Still — could this be their year? Very loose “maybe.” Just make sure you’re checking for the best lines if you’re betting on these guys because their odds are bouncing around with every game.
The Long Shots (a.k.a. Don’t Put the Mortgage On It)
Some Canadian teams are technically still in the race, but it’s more like that scene in a horror movie where the guy says “I think we lost him!” right before the monster eats him.
- Ottawa Senators made it up to around +20000. They were knocked out by the Leafs though.
- Montreal Canadiens? Were +11000 or worse. This isn’t 1993. They were knocked out of contention by the caps.
- Calgary Flames and Vancouver Canucks didn’t make the cut.
There’s always a potential miracle run lurking in hockey (see: 2021 Canadiens), but for these teams? It would take a Disney-level miracle and a whole lot of goalie magic.
A Cold, Hard Truth: No Canadian Cup Since 1993
I was a young football fan in 1993 when The Canadiens took down Gretzky and the Kings. I was more worried about Ninja Turtles than who hoisted the Stanley Cup.
Fast-forward to now: I’ve seen rent prices rise, crypto rollercoaster up and down, and Connor Bedard get drafted, but I haven’t seen a single Canadian team win it all.
There Have Been Some Close Calls
Since ‘93, Canada has been chasing the dragon. But it’s not like there haven’t been some close calls:
- Vancouver in 1994 – Lost to the Rangers in game 7.
- Calgary in 2004 – That non-goal in Game 6 still haunts Flames fans.
- Edmonton in 2006 – Roloson goes down, and the Hurricanes take Game 7.
- Ottawa in 2007 – Anaheim flattened them in 5.
- Vancouver again in 2011 – Lost in 7, then the riot. Brutal.
- Montreal in 2021 – Pandemic miracle run, then boom — Tampa.
- Edmonton in 2024 – Forced a Game 7 after being down 0–3, only to fall short to Florida.
Each time, Canada gets their hopes up. And each time, the Cup ends up in a sunbelt city where ice is more of a suggestion than a reality.
Why Canada Keeps Coming Up Empty
From the outside looking in, it’s kind of wild. The NHL’s biggest fanbases are in Canada. Every kid there grows up on skates. So what gives? Why can’t Canada pull a Stanley Cup for the last 32 years?
People love to throw around theories. Here are a few I actually buy:
Inequality
The salary cap and exchange rates make it harder to hoard talent. No more stacked Canadian dynasties like the ’80s Oilers or ’70s Habs.
US Expansion
More U.S. teams equals more good U.S. teams. And when you’re facing the Lightning, Bruins, or Avalanche every year? Good luck.
Fan Pressure
Canadian fans are intense. The Leafs playing a Game 7 at home, is like defusing a bomb with 20,000 people screaming in your face. That’s not easy.
Betting on the Drought to End? Where’s the Best Value?
If you believe that Canada can take it, and you want to throw a few bucks down, which sportsbooks offer the best value? Historically, offshore books tend to hang longer odds on Canadian teams.
If you’re taking the front-running Oilers at the moment, you get an extra $20 at Mybookie over the other books I’m tracking. So head offshore.
If you want the Leafs or the Jets, you can find better odds at regulated books if you’re in the right state to use them. If not, then offshore is still your best, and only, bet.
Bottom line? If you’re chasing value and you’re comfortable betting offshore, you can usually find a better number — especially on long shots or polarizing teams. Just make sure the site is reputable, and always, always check lines at more than one sportsbook to get the best value.
My Gut Feeling?
Honestly? I don’t know. The drought’s real. The pressure’s heavy. But hockey’s weird, and sometimes weird is all you need.
If I were betting this time around (I’m not), I’d for sure ride with the Oilers out of the Canada bunch at this point. They’ve got the talent, the firepower, and a chip on their shoulder from last year. But I wouldn’t be shocked if we’re sitting here in June watching the Rangers or Avs skate around with Stanley again.
That said — if a Canadian team finally pulls it off, I’ll be happy for our neighbors to the north. You guys brought us the game after all, you deserve a cup once in a while.
Over to You
Alright, your turn. After 30+ years, can the country that lives and breathes hockey finally bring the Cup home? The Oilers look ready, the Leafs are lurking, and the Jets might just surprise us all.
What do you think — is this the year Canada breaks through, or are they in for more heartbreak?
Drop your thoughts in the comments or argue with me on Twitter. I’m here for all of it.
About the Author
Alonzo Solano
The Boss of Betting, Editor-in-Chief & Sports Analyst
Alonzo Solano is an author, sports analyst, Editor in Chief of BossofBetting.com, and host of the 'NFL Latino TV' podcast.
Outside of family, his biggest passion is NFL football. Perhaps he is best known for his podcast 'NFL Latino TV,' where he shares his analysis and perspectives on the game with a worldwide Spanish-speaking audience.
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