The Most Successful Canadian Hockey Teams in the NHL

Officially commencing play with the 1917/18 season, the NHL has always had a strong Canadian presence.

From its inception through the Original Six Era, and to the early ‘90s, teams north of the border continued to stack up more and more championships.

Since the Montréal Canadiens hoisted Lord Stanley in 1993, however, the title has evaded the most hockey-avid nation on the planet. Five other Canadian teams have gone to the Stanley Cup Finals since, but to no avail.

For The 29th Year In A Row, Canada Has Lost The Stanley Cup https://t.co/3Y0qryXiZB pic.twitter.com/TYSd5NAFJY

— Barstool Sports (@barstoolsports) June 13, 2022

Regardless, the history of Canadian hockey teams in the NHL continues to shine. 

On this page, you’ll find the most successful Canadian hockey teams in the NHL ranked by their championships, appearances in the final stage, and postseason appearances. 

NHA and former franchise location records are noted but not included in postseason records or final rankings.

Montréal Canadiens

• Inaugural NHL Season: 1917/18

• Stanley Cup Wins: 23

• Finals Appearances: 33

• Postseason Appearances: 85

The Montréal Canadiens are the most successful Canadian hockey team to ever feature in the NHL. Furthermore, their 23 Stanley Cup wins hold the Habs as the most successful NHL team of all time outright.

For decades, the Canadiens were one of the most competitive teams in the NHL, which was epitomized by their five-season streak of Stanley Cup wins from 1956 to 1960.

• Greatest Canadian NHL Players of All Time

You could also add the pre-NHL success of the Habs in the NHA to further solidify them as the very best Canadian team. In this precursor league, Montréal won the Cup once, following two trips to the finals and three postseason appearances. 

As the 1993 Stanley Cup champions, the franchise remains the most recent Canadian team to win it all. They’ve also come the closest most recently, making it to the finals in 2021.

Toronto Maple Leafs

• Inaugural NHL Season: 1917/18

• Stanley Cup Wins: 13

• Finals Appearances: 21

• Postseason Appearances: 71

While the modern-era Toronto Maple Leafs are still trying to make a name for themselves, the Buds have a history of dominance to rank among the most successful Canadian hockey teams in the NHL. 

Highlighting the franchise’s decorated hockey history, Toronto won a three-peat of Stanley Cups in the 1940s and then again in the 1960s. 

This season, the Maple Leafs are certainly in contention to add to the franchise’s incredible legacy and snap Canada’s winless streak.

In the ice hockey odds, Toronto is the second favourite at +850 to win the Stanley Cup. Maybe this is the season that Canada finally welcomes the coveted trophy back to the north.

Edmonton Oilers

• Inaugural NHL Season: 1979-80

• Stanley Cup Wins: 5

• Finals Appearances: 7

• Postseason Appearances: 24

Four of the five times that the Edmonton Oilers have earned an engraving on the bands of the Stanley Cup, it was with Wayne Gretzky leading the charge. In 1990, though, a Mark Messier-led Oilers landed the fifth. 

Even without The Great One’s wins, Edmonton would still stand third on this list of the most successful Canadian hockey teams in the NHL.

Looking to add the team’s second non-Gretzky trophy, Connor McDavid and Leon Draisaitl now lead the Oilers.

As demonstrated by online sports betting markets, the rest of the roster will need to step up for Edmonton to challenge seriously this season, sitting out at +1300 to win the Stanley Cup.

Calgary Flames

• Inaugural NHL Season: 1980/81

• Stanley Cup Wins: 1

• Finals Appearances: 3

• Postseason Appearances: 25

As the Flames franchise based in Calgary, they went all the way in 1989, beating the Canadiens 4-2 in the Stanley Cup Finals to avenge the loss to their compatriots in the final series of 1986. 

Prior to moving to Calgary, they were the Atlanta Flames, down in Georgia. The US-based team started play in the NHL for the 1972/73 season, making it to the postseason six times before heading north in 1980.

In the face of the complete capitulation of the roster, general manager Brad Treliving ended up putting on one of the best offseason performances in the NHL, allowing the Flames to remain as contenders this season.

Vancouver Canucks

• Inaugural NHL Season: 1970/71

• Stanley Cup Wins: 0

• Finals Appearances: 3

• Postseason Appearances: 28

Regular champions in the WHL, the Vancouver Canucks have struggled to replicate such success in the NHL. That said, three builds have come very close to getting Vancouver inscribed on the Stanley Cup. 

In 1982, 1994, and 2011, the Canucks made it to the Stanley Cup Finals, with only the ‘80s run not going to Game 7.

Ottawa Senators

• Inaugural NHL Season: 1992/93

• Stanley Cup Wins: 0

• Finals Appearances: 1

• Postseason Appearances: 16

For these rankings, only the modern incarnation of the Ottawa Senators was considered. A fairly young franchise, the Sens made it to the 2007 Stanley Cup Finals, but lost 4-1 to the Anaheim Ducks. 

The Original Ottawa Senators, as they’re now known, aren’t considered to be a part of this current Senators’ franchise history. Still, they represented the city very well in their day.

Starting play in the NHA in 1909/10, the Original Senators went to four postseasons, lost in one final, but won four Stanley Cup Challenges.

In the NHL, from the 1917/18 season, they went to ten postseasons, four finals, and won the Stanley Cup four times before relocating to St. Louis in 1934 as the Eagles – folding in 1935.

Québec Nordiques

• Inaugural NHL Season: 1979/80

• Stanley Cup Wins: 0

• Finals Appearances: 0

• Postseason Appearances: 9

The market that craves an expansion team the most – despite the presence of the Canadiens – when Québec was contending in the NHL, the Nordiques put in some strong seasons after passing over from the WHA. 

WHA champions in 1977, the Nordiques climbed to the NHL postseason on nine occasions, falling at the penultimate hurdle in 1982 and 1985.

In 1995, the franchise became the Colorado Avalanche, winning the Stanley Cup three times since.

Winnipeg Jets

• Inaugural NHL Season: 2011/12

• Stanley Cup Wins: 0

• Finals Appearances: 0

• Postseason Appearances: 5

The young Winnipeg Jets looked to be building a formidable unit through the early 2010s, but have struggled to recapture the momentum and presence that took the promising team to the 2017/18 Western Conference Finals. 

Prior to becoming the Jets in Canada, the franchise was the Atlanta Thrashers. As the Thrashers, they competed in the NHL from the 1999/20 season, only ever qualifying for the postseason once before coming north.

Before them, there was another team in Winnipeg. The Original Winnipeg Jets entered the NHL in 1979, earning 11 postseason berths before relocating the Phoenix, Arizona, in 1996, where the franchise remains to this day.

A Canadian team stands as the most successful in the history of the NHL, but it’s the modern drought that dominates headlines when the Stanley Cup Playoffs come around each season.

*Credit for all images in this article belongs to AP Photo*

FIRST PUBLISHED: 7th October 2022