Last time a Canadian team won the Stanley Cup was in 1993 when Montreal Canadiens defeated Los Angeles Kings scoring 4 goals.

However, since then, no teams from Canada have been able to grab one of the most revered trophies in all of the sports, despite coming close several times. 

It has been three decades since the last time a Canadian team lifted the Stanley Cup, and the dry spell has left Canadian hockey fans longing for a victory. Canada Stanley Cup drought has become NHL's longest on record.

Despite winning the Stanley Cup a record 23 times, ten more than the second Toronto Maple Leafs, Montreal has struggled to maintain the same level of success they enjoyed in the past.

The Canadiens, who have had their share of highs and lows, is also the most recent Canadian team to make it to the Stanley Cup Final in 2021, but they lost, 4-1, to the Tampa Bay Lightning.

Teams With Longest Stanley Cup Droughts

Teams with the longest championship droughts are

  • Toronto Maple Leafs - 56 years
  • Buffalo Sabres - 52 years
  • Philadelphia Flyers - 48 years
  • New York Islanders - 40 years
  • Calgary Flames - 34 years
  • Edmonton Oilers - 33 years
  • New York Rangers - 29 years

The Toronto Maple Leafs, formerly known as the Toronto St. Patricks, currently holds the dubious distinction of having the lengthiest dearth of Stanley Cup victories among all NHL franchises.

It has been 56 years since they last tasted the victory of lifting the championship in the 1966-67 season.

It is a well-established fact that Canadian teams have a superior track record of winning the title in the past. Still, the northern US border nation has found it challenging to secure the championship in the contemporary era.

Maple Leafs 1966-67 winner team photo
Source : instagram

Several NHL teams from Canada, the Canadiens and the Oilers have recently struggled to win the coveted trophy. And for the Maple Leafs, the condition is far worse as the drought continues. 

For their fans, it is heartbreak every year as there has not been much to celebrate since their last Stanley Cup win in 1967. The 4-2 triumph over the fellow Canadian team Montreal, led by head coach Punch Imlach was not just their last NHL Finals win but also the last time they reached the finals.

The Maple Leafs have not recorded any wins in the playoff series since 2004 until the 2023 first-round playoff, where they defeated Tampa Bay 4-2 to win the series.

Similarly, Buffalo Sabres have been closely following the Maple Leafs as they hold second place in teams with the longest Stanley Cup droughts. The Sabres have been searching for another NHL finals victory since their last triumph in 1971, spanning over half a century.

On the other hand, the Philadelphia Flyers, who have two Stanley Cup Finals wins, are the third team with the most extended Stanley Cup droughts in 48 years.

After head coach Fred Shero ushered the team to back-to-back NHL championship victories in 1974 and 1975, the Flyers lost their charm and have not won since then. 

Flyers' Terry Crisp with the Stanley Cup in 1975
Source : twitter

Despite making it to the finals on six occasions after their memorable victory in 1975, the Philadelphia team has been unable to repeat their success, failing to win the championship every time they have reached the finals.

According to Statmuse, other teams with the most prolonged championship dearth are the New York Islanders for 40 years, Calgary Flames for 34 years, and Edmonton Oilers for 33 years. 

Likewise, the last time Carolina Hurricanes won the Stanley Cup was in 2006, whereas Seattle Kraken and the Vegas Golden Knights have yet to win the championship.

Canadian Teams To Win Hockey Championship

Last Canadian team to win the Stanley Cup was the Montreal Canadiens in 1993. Montreal secured a comfortable 4-1 win against the Los Angeles Kings in the finals.

Out of seven Canadian NHL franchises, three teams, the Ottawa Senators, Winnipeg Jets, and Vancouver Canucks have never won the Stanley Cup. Hockey is more than just a game in Canada, and it has been an embarrassingly long time since a Canadian team has hoisted the cup.

  • Montreal Canadiens - 1993
  • Edmonton Oilers - 1990
  • Calgary Flames - 1989
  • Toronto Maple Leafs - 1967

Although two Canadian teams, Montreal and Toronto, hold the top positions in the list of most Stanley Cup Finals wins with 23 and 13 victories, respectively, they have struggled to replicate their past success recently.

The Canadiens All-Star team from the 90s including Guy Lafleur
Source : facebook

The Oilers and Maple Leafs are the only teams left representing Canada in the 2022-23 NHL campaign as they head to the second round of playoffs. Could one of the two break the 30 years dry spell and bring the coveted Stanley Cup to Canada this time? Only time will tell.

The Canadiens' success in the early 1990s was attributed to their commitment to building a solid team, which included key players like Patrick Roy, Vincent Damphousse, and Kirk Muller.

Head coach, Jacques Demers, was also crucial to their victory, motivating and leading the team to their 1993 Stanley Cup win against the Los Angeles Kings.

Besides, the Edmonton Oilers' victory over the Bruins in 1990 remains their last Stanley Cup trophy, whereas Calgary Flames won their final championship in 1989. 

Furthermore, to find the Maple Leafs, one has to peddle back even more to 1967. In the era where Canadian teams dominated the league, Toronto won three-peat in 1962 and 1963, followed by another title win in 1967. 

Canadian ice hockey star Luke Green in the Winnipeg Jets kit, February 2021
Source : instagram

But little did they and their fans know that it was the end of their golden era and there would be a prolonged wait for their subsequent Stanley Cup victory.

Teams From Canada Without An NHL Championship

  • Ottawa Senators
  • Winnipeg Jets
  • Vancouver Canucks

The Senators, Jets, and Canucks are three teams from Canada that have never won the Stanley Cup. Vancouver came close to winning their first trophy in 2011 but had to comprise in a heartbreaking defeat against the Boston Bruins in Game 7. 

On the flip side, the Ottawa Senators and the Winnipeg Jets have never in NHL history made it to the finals, let alone win the Stanley Cup. 

The Last Time The Toronto Maple Leafs Won A Stanley Cup

Toronto Maple Leafs last won a Stanley Cup 56 years ago in 1967. It was an All-Canadian finals as the Maple Leafs took on the Canadiens in the best-of-seven series format.

Through Montreal made an impressive start with a 6-2 thumping win in the first game taking a 1-0 series lead, Toronto went on to win the finals in Game 6 on May 2, 1967, clinching the series by 4-2.

Can Maple Leafs end the curse this season?
Source : instagram

The 1967 finals were quite memorable, mainly for Canadian hockey fans, because that was the epitome of the dominance of Canadian teams in the NHL.

Toronto's championship drought in the NHL has extended to 56 years following their last appearance in the Stanley Cup Finals. Fans remain hopeful that the Leafs will one day hoist the Cup again, even though the team has not won a championship in over 50 years.

Golden Era 40s to 60s

The Maple Leafs, originally known as the Toronto Arenas, is one of the teams of the Original Six NHL. During the 1940s, the Leafs had some of their greatest successes, winning five Stanley Cup championships.

The team was led by star players such as Teeder Kennedy and Turk Broda, one of the league's top goaltenders. Bill Barilko was another standout player for the Leafs, scoring the Cup-winning goal in 1951.

In the 1960s, the Leafs continued their success, winning four Stanley Cup championships during the decade. The team was again led by top players like Johnny Bower, who won the Vezina Trophy twice during the decade. Tim Horton was another key player for the Leafs, known for his physical play.

Maple Leafs Downfall Since the 70s

In the 1970s, the Toronto Maple Leafs' glory years gradually faded, and they have not reached the final since their last victory. The team's fortunes began to decline, and they went through a rebuilding period.

Toronto defeated Tampa Bay to advance to the 2nd Round of playoffs in 2023
Source : nhl

Then starting with the 1980s and 1990s, the Maple Leafs struggled to win the Stanley Cup, despite having talented players such as Doug Gilmour and Wendel Clark. They made it to the playoffs several times but couldn't quite get over the hump.

In the 2000s, the Maple Leafs went through another rebuilding phase, struggling to find consistency and rarely making it to the playoffs. Their last playoff appearance was in the 2022-23 season led by Auston Matthews and they have not lifted the Stanley Cup since 1967.

When Was The Last Time Edmonton Oilers Won A Stanley Cup?

The last time Edmonton Oilers won the Stanley Cup was 33 years ago in 1990. Their fans have been yearning for another championship victory ever since.

Oilers were sharp from the beginning of the series against the Bruins in the 1990 Stanley Cup Finals, as they took a 2-0 lead in the first two games.

Although they lost the third game of the series by a small margin, they easily won the remaining two games. Edmonton went on to win the series 4-1.

The 1990 Stanley Cup Oilers team photo
Source : twitter

Despite being founded relatively late compared to other franchises, the Edmonton Oilers made a swift ascent to become one of the league's most impressive and dominant teams.

Led by all-time greats Wayne Gretzky, Mark Messier, and Jari Kurri, the Oilers won five Stanley Cups in seven years.

But since their last championship win in 1990, they have stumbled hard to return to championship form, leaving many fans wondering when they will see their team again hoist the Stanley Cup.

The Drought Began After A Trade

The Oilers' dynasty ended in the early 1990s, as Center Gretzky was traded to the Los Angeles Kings in 1988, and other key players also left the club.

The team struggled to find their groove in the 1990s, missing the playoffs in five of the ten seasons in the decade. Edmonton did have some success in the early 2000s, making it to the Stanley Cup Finals in 2006 before falling to the Carolina Hurricanes. 

Oilers defenseman Chris Pronger in 2006 playoffs
Source : youtube

However, the team's performance was inconsistent in the following years, missing the playoffs in eight of the next ten seasons.

The Oilers have made the playoffs three times in the last decade but have failed to advance past the second round. Despite this, the team remains hopeful for the future and looks to build on their recent successes to bring the Stanley Cup back to Edmonton.

Besides, the Oilers are through to the NHL second-round playoffs of the 2022-23 campaign, as they got the best of the Los Angeles Kings, winning the series 4-2. They will face the Golden Knights in Round Two.