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While hockey might not be the most popular sport within the Big Four, it certainly has a special trophy. Virtually everyone who’s played the ice game has dreamed of lifting the Stanley Cup; that’s especially true for Canadians who, at the risk of indulging in a stereotype, grow up skating on rinks, ponds, and any frozen surface in between.

And while Canada, as a whole, loves hockey, finding postseason success is another story. Despite the multiple franchises — some of which boast incredible histories — a Canadian NHL team hasn’t claimed a Stanley Cup in quite some time.

Just how long? Let’s break it down.

Who was the last Canadian team to lift the Stanley Cup?

Over the years, the Montreal Canadiens put together arguably the richest history in the NHL. In that vein, it’s fitting that the Habs were the last Canadian club to win the Stanley Cup.

That victory came during the 1993 Stanley Cup Finals. The Canadiens had a strong regular season but entered the playoffs as the third seed from the Adams Division. While that could have set up a tricky postseason path, Montreal was aided by some other results. After dispatching the Nordiques in the first round, they met the Buffalo Sabres — who upset the top-seeded Bruins — in the second round. Then, in the Eastern Conference Finals, the Canadian club met the New York Islanders, who had finished third in the Patrick Division.

That saw the Canadiens reach the Stanley Cup Finals, where they met an LA Kings squad that finished third in the Smyth Division. And while the presence of Wayne Gretzky and his running mates may have been intimidating, Montreal held firm. After dropping Game 1, the Habs rattled off four victories to claim the title.

The Stanley Cup had returned to Canada; little did anyone know that it wouldn’t be back for decades.

Historically, Canadian teams have won plenty of Stanley Cups

When you hear that a Canadian team hasn’t won a Stanley Cup since 1993, you might think that the nation has a disappointing hockey history. While that may be true in recent years, it isn’t the case when you zoom out further. In fact, the two most successful franchises, at least in terms of championships, hail from the Great White North.

Consider the following table:

TeamStanley Cup Titles
Montreal Canadiens24
Toronto Maple Leafs13
Edmonton Oilers 5
Calgary Flames 1
Ottawa Senators0
Winnipeg Jets0
Vancouver Canucks0

There are, however, some caveats to that table. The original Ottawa Senators were rather successful and won four Stanley Cups, but those successes don’t count toward the current franchise’s resume. Some other defunct teams — the Montreal Maroons (two titles), the Vancouver Millionaires (one title), and the Victoria Cougars (one title)– also lifted the Cup.

Canada’s desire for a Stanley Cup hasn’t faded, but the odds aren’t in their favor

Fans outside of the Scotiabank Arena ahead of a Toronto Maple Leafs game.
Toronto Maple Leafs fans are still holding out hope of winning the Stanley Cup. | Steve Russell/Toronto Star via Getty Images

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When you consider a drought that began in 1994, you might think that Canada has collectively become cynical when it comes to the Stanley Cup playoffs. And while there’s certainly room for that — the Toronto Maple Leafs, in particular, have put their fans through the postseason wringer — there’s still a sense of solidarity. Once your favorite team is eliminated, it’s time to pull for the other Canadian clubs.

“I think in Canada, we cheer for our particular NHL team.” Gord Stellick, sports commentator and former Toronto Maple Leafs general manager, told Global News in 20178 after the final Canadian team was eliminated from Cup contention. “But we also cheer for the other Canadian based teams because this has been a drought that’s been a little too long. If you spun the roulette wheel over 25 years, with one in 5 odds, you should have got a Stanley Cup.”

So what’s behind that drought? Whether Stellick intended it or not, the roulette analogy hits pretty close to home. It all comes down to randomness and the numbers game.

First and foremost, there simply aren’t that many Canadian teams in the NHL. When you consider that several play in the same division — Toronto, Ottawa, and Montreal, for example, are in direct competition — that further reduces the chances of getting the maximum number of clubs into the postseason.

So let’s say it’s been a good year, and Canada gets four teams into the playoffs. That provides a 25% chance of winning the Cup, but that’s still not a surefire ticket to success. Not only will those clubs eventually play each other, but hockey is a notoriously random sport, especially in the postseason. Even if a Canadian team is the nominal favorite, it could be sunk by a bad bounce, running into a hot goalie, or any other form of puck luck.

It’s also worth considering other ways that the numbers can make things tougher on Canada. Beyond playoff berths, there are also better chances of star players landing on American teams. Talent, by and large, wins out.

That won’t stop Canada from collectively doing what it can to bring the Stanley Cup back north of the border, though. Only time will tell how long the wait will last.