The Montreal Canadiens confounded NHL betting oddsmakers last year, reaching the Stanley Cup Finals before eventually falling to the two-time champion Tampa Bay Lightning in 5 games. That loss extended Canada's Cup drought. No Canadian team has won the Stanley Cup since the 1993 Habs.

The Canadiens were +2600 at FanDuel to win the Stanley Cup before the 2021 NHL season began. Canadiens bettors were rewarded for their pluck throughout the playoffs until the Finals. The Habs were +180 underdogs heading into their first playoff series against the Maple Leafs. Montreal was +107 to advance past Winnipeg in the second round of the playoffs and +124 to beat Las Vegas and reach the Final at several sports betting sites.

As we approach the NHL playoffs in the 2021-22 season, the Canadiens will be on the outside looking in. Bottom of the Atlantic Division, their hopes for the Stanley Cup on NHL futures markets have already turned to next year. The top Canadian team in terms of betting odds to win the Stanley Cup in 2022 is the Calgary Flames, who are +900 at DraftKings Ontario.

With Ontario sports betting now live in the province as of Monday, it's an exciting time for sports betting in Canada. The Toronto Maple Leafs, currently behind the Florida Panthers in the Atlantic Division, are +1200 at DraftKings Ontario to win the Stanley Cup right now.

Ranking Top Stanley Cup Champs From Canada

That Montreal was an upstart challenger against a team from the Gulf Coast of Florida last season is a perfect metaphor for just how much the NHL has changed in the 50+ seasons since it first expanded in 1967. Since the Original Six became the Dirty Dozen, 16 teams in the Great White North have hoisted the Stanley Cup. There were seven straight Stanley Cups won by Canadian teams from 1984-90 but no team from Canada has won the NHL’s top prize in 28 years.

Wayne Gretzky, Guy Lafleur, Larry Robinson, Ken Dryden, Mark Messier and Denis Savard were among the players who have won Cups for Canada in the past six decades.

Here are the top seven Stanley Cup winners based in Canada since the NHL expanded 54 years ago. They are listed with their odds to win the Stanley Cup Final when available.

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1. 1970-71 Montreal Canadiens

   Montreal was a decisive underdog in Round 1 of the playoffs against the Big Bad Boston Bruins, who had swept the Blues to win the 1970 Stanley Cup and were led by Bobby Orr and Phil Esposito. The Canadiens entered the postseason with an unheralded goaltender who was originally drafted by the Bruins and had played just six games since being called up as “insurance” late in the season. But Ken Dryden stopped Boston’s big guns in an epic seven-game series. He would go on to Hall of Fame career and win six Cups, all with Montreal.

2. 1983-84 Edmonton Oilers

   Gretzky – also known as Janet’s hubby, Paulina’s dad and the grandfather of Dustin Johnson’s children – led a loaded Oilers team. Edmonton stopped a four-year title streak in Nassau County, New York by toppling the champion Islanders in the Stanley Cup Finals.

   The first Stanley Cup 1984#Oilers #NewSeason pic.twitter.com/fUEw4QmF5G

   — Vintage Oilers (@VintageOilers) September 12, 2019

   Four different Oilers – none of them Gretzky – scored the game-winners as Edmonton became the first former WHA team to win a Stanley Cup after just five seasons in the NHL.

3. 1977-78 Canadiens

   These Canadiens rampaged through the first two rounds of the playoffs – going 8-1 – after losing just 10 games in the regular season. Another matchup against Boston produced a similar result – with the Habs taking the Cup in six games. This would be Montreal’s third of four consecutive Stanley Cups.

4. 1987-88 Oilers

   Stanley Cup Final Odds: -340

   Gretzky’s final season in Canada was capped off with the Oilers’ fourth Cup in five seasons. Edmonton bottomed out at +300 to win the Cup before the playoffs began. Its playoff rampage was interrupted by a power outage at old Boston Garden during Game 4 of the Finals, which would be suspended. The Oilers would go on to earn the “sweep” of the Bruins in Game 5.

   August 9, 1988: The Edmonton Oilers trade Wayne Gretzky to the Los Angeles Kings. pic.twitter.com/JOyPimYlqk

   — This Day In Sports Clips (@TDISportsClips) August 9, 2020

   On Aug. 9, 1988, Peter Pocklington committed the unforgivable sin of shipping Gretzky to the Los Angeles Kings. (Yes, Gretzky wanted to go to LA and he was not going to re-sign with Edmonton. But the pain lingers.) The Great One would never win another Cup while playing for the Kings, New York Rangers or St. Louis Blues. The Oilers, meanwhile, would win their fifth – and most recent Cup – in 1990.

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5. 1986-87 Oilers

   Stanley Cup Final Odds: -240

   This version of the Oilers opened at +150 to win the third Cup in four years for the franchise. Mission accomplished. Edmonton went 12-1 after losing its playoff opener to reach the finals against the Philadelphia Flyers. The mid-1980s version of the Broad Street Bullies took the Oilers to seven games in the Finals before Glenn Anderson’s late tally in Game 7 iced the title. Gretzky would nab his second Conn Smythe Trophy as playoff MVP after amassing 13 points in the Finals.

6. 1976-77 Canadiens

   Loaded with legends like Jacques Lemaire, Lafleur, Robinson and Dryden, the 1976-77 Montreal Canadiens triggered a dominant rampage throughout the NHL that resulted in four consecutive Stanley Cups.

   

   Montreal went 60-8-12 in the regular season and 12-2 in the postseason games en route its championship. Dryden would post four shutouts in the playoffs and Lafleur led the way with nine goals and 17 assists in just 14 games to win the Conn Smythe Trophy.

7. 1984-85 Oilers

   Stanley Cup Final Odds: -160

   This version of the Oilers was named the Greatest NHL Team ever by the league and its fans in 2017. And for good reason. In winning Edmonton’s second straight title, the Oilers surpassed their sky-high preseason expectations and rolled through the playoffs, going 15-3. Gretzky scored 73 goals and notched an NHL-record 135 assists for 208 points in the regular season. He would add 49 points – another record – in the playoffs. Four of Edmonton’s top-five scorers that season – Jari Kurri (19 playoff goals & four hat tricks), Mark Messier, Anderson and Gretzky – landed in the Hockey Hall of Fame.

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