The Montreal Canadiens and Toronto Maple Leafs are the two most successful teams in NHL history, with 24 and 13 Stanley Cup wins respectively.

However, not since the Canadiens’ last triumph in 1993 have a team from North of the United States lifted the big prize.

Close Encounters

As many as eight Canadian teams have been in the 26 NHL seasons since the Canadiens last lifted the trophy for the country.

There have been a couple of close encounters though – Vancouver was heartbroken in a 3-4 defeat to the Boston Bruins in 2011. The same happened in 1994 to the New York Rangers.

The Edmonton Oilers and Calgary Flames lost by the same score in the seven-game Stanley Cup series in 2004 and 2006, whilst the Ottawa Senators also reached the final in 2007.

Where Has It All Gone Wrong?

The Toronto Maple Leafs were successful in the 1940s and 1960s, winning nine of their 13 Stanley Cups in those two decades combined. They haven’t even reached the final since their last final in 1967, let alone won it.

If anything, they are Canada’s best hope for the 2021 season and have made an impressive start to back it up. In fact, if you look at their odds to win the Stanley Cup with Canadian online casinos, they are generally fourth favourites with a price of 9/1.

Only the Colorado Avalanche, Vegas Golden Knights and defending champions Tampa Bay Lightning have shorter odds currently.

Not since the 2004-05 season have they won a playoff game though and with the unique schedule this season, where they only face divisional opponents, who are the other Canadian teams, it’s hard to judge where they really are before the knockout stages later this year.

Indeed, the Maple Leafs lack depth in defence and the goaltending hasn’t been too consistent in the opening months either.

The Winnipeg Jets are currently sitting in second place in the North Division. Formerly known as the Atlanta Thrashers, the Jets were awful last season but have an impressive goaltender in Connor Hellebuyck.

There’s not too much praise for the rest of the team but Mark Scheifele, Nikolaj Ehlers and Kyle Connor have all helped the franchise to where they are 33 games into the 2020-21 campaign. Will they be able to hold up though?

The Edmonton Oilers made the playoffs in each of their first 13 NHL seasons when they had the likes of Wayne Gretzky, Mark Messier, Paul Coffey, Jari Kurri, Glenn Anderson and Grant Fuhr.

Those days are long behind now. And despite drafting some top talents including Connor McDavid and Leon Draisaitl, they have somewhat embarrassingly failed to build a team around them capable of competing for the ultimate prize in the sport.

Only the top three teams from each division will make the playoffs this year and there is a gap starting to open up between the top three in the North Division and the Montreal Canadians in fourth.

Montreal were the number 12 seed in the playoffs last season and even upset the Pittsburgh Penguins. But poor investment in the roster over the off-season makes it feel as though the franchise took a step backward heading into the new campaign. Results on the ice are starting to back that up.

The Vancouver Canucks have started to turn the corner in March having gone 2-9-2 in February. 21-year-old Quinn Hughes is an assist machine and Elias Pettersson, only one year his senior, is producing the goods. However, the squad does lack depth and has arguably spent too much money on its backups.

With just one playoff win since the 2005 lockout, the Calgary Flames aren’t doing their country any favours. A number of top defensemen have been moved on over the past couple of seasons and it’s starting to show – 102 goals shipped in 34 matches as they’ve lost more than they’ve won as we approach the end of March.

Propping up the North Division, or the Canadian Division, whichever you’d prefer to refer to it as, are the Ottawa Senators. Easily the worst team north of the border and one of the worst in all of hocky. Finishing in the bottom two in each of the past three seasons has seen a number of exciting youngsters drafted, including efenseman Thomas Chabot, winger Brady Tkachuk, and electric German rookie Tim Stuetzle. Some may feel the future is bright for Ottawa, but the owner has shown us how not to run a franchise.