Canadian Stanley Cup drought reaches 30 years

June 9, 2023, marks the 30-year anniversary of the Montreal Canadiens beating Wayne Gretzky and the Los Angeles Kings to win the Stanley Cup for the 24th time in franchise history. The date will also mark 30 years since a Canadian team has lifted the Stanley Cup.

This is by far the longest time between Stanley Cup wins for Canadian franchises, with the previous “drought” being six seasons, between Cup wins for the 1935 Montreal Maroons and 1942 Toronto Maple Leafs.

It looked like a Canadian team would have a good chance to lift Lord Stanley’s Mug this season, with the Toronto Maple Leafs finally exorcising their first-round demons by beating the Tampa Bay Lightning, and the Edmonton Oilers boasting arguably the two best players in the NHL.

However, it was not to be as the Leafs fell to the finals-bound Florida Panthers in five games, while Connor McDavid, Leon Draisaitl, and the Oilers were ousted from the second round by the Vegas Golden Knights. 

Five Canadian teams have made it to the Final over the past 30 years, but each has failed to bring the Cup home to Canada.

As the Panthers and Golden Knights battle for the first Stanley Cup title in their respective franchise histories, TSN.ca looks at each Canadian team’s best run at the Cup since the Canadiens last brought the cup North 30 years ago.
 

Montreal Canadiens - Last Stanley Cup: 1993

Best playoff appearance since last Stanley Cup: 2020-21 Stanley Cup Final - Lost to Tampa Bay Lightning (4-1) in 2020-21

Montreal CanadiensThe last Canadian team to win the Stanley Cup made a Cinderella run to the Final in 2021 but was unable to unseat the defending champion Lightning, losing in five games in what was the final NHL season of captain Shea Weber’s career and the last healthy season for goaltender Carey Price. The former Vezina and Hart Trophy winner would play just five games the following season due to a knee injury. 

With the COVID-19 pandemic impacting the NHL for a second straight season, including cross-border travel, the league temporarily realigned and placed all the Canadian teams in one division for the 2020-21 season. The Canadiens fired head coach Claude Julien midway through the year, replacing him with Dominique Ducharme, and just squeaked into the postseason with a 24-21-11 record.

The team caught lightning in a bottle in the playoffs, coming back from a 3-1 deficit to beat the Maple Leafs in the first round before sweeping the Winnipeg Jets in the second round. The Habs would reach the Final after knocking off the Golden Knights in six games.

Montreal forward Brendan Gallagher said the circumstances created by the pandemic helped the team bond through their long playoff run.

"One cool thing I'll say that came with all the COVID-19 brutalness was when we would win a series, you'd just be with your teammates," Gallagher told the Canadian Press, in a story published on May 19. "There was no going out celebrating. We stayed in the locker room; we had pizza and beer, and you'd just sit and hang out.

"It was those special moments."

Montreal finished 2022-23 with the fifth-worst record in the NHL and the worst record amongst Canadian teams. With Price all but retired, the Habs will look to rebuild and move forward with a young core, led by captain Nick Suzuki and sharpshooter Cole Caufield, as they attempt to win the 25th Stanley Cup in franchise history.

Edmonton Oilers - Last Stanley Cup: 1990

Best playoff appearance since last Stanley Cup: 2005-06 Stanley Cup Final - Lost to Carolina Hurricanes (4-3)

Edmonton OilersThe Oilers' most successful playoff run over the past 30 years did not come with Hart Trophy winners McDavid and Draisaitl at the helm, but rather in 2005-06 when they, like the 2021 Canadiens, made a storybook run to the Cup Final as a No. 8 seed. 

Led by the off-season acquisition of former Norris Trophy winner Chris Pronger and the trade deadline acquisition of veteran goaltender Dwayne Roloson, the Oilers upset the Presidents’ Trophy-winning Detroit Red Wings in the first round and proceeded to beat the San Jose Sharks and Mighty Ducks of Anaheim on their way to the Stanley Cup Final. 

"Every person in that city was just completely absorbed," former Oilers forward Shawn Horcoff told the Canadian Press of Edmonton during the team’s Cup Final run. "The only thing on anybody's mind." 

Roloson went 12-5 with a .927 save percentage and a 2.33 goals-against average during the Oilers’ playoff run and, along with Pronger, was a Conn Smythe Trophy favourite heading into the Final. Unfortunately, he would go down with an injury in Game 1 and would not return for the remainder of the series. With Jussi Markkanen as the new starter, the Oilers were able to push the Hurricanes to a Game 7 after trailing 3-1 in the series but were unable to win the deciding game.

Horcoff, who scored 73 regular-season points and added seven goals and 19 points during the playoff run, said the pain of losing Game 7 has not gone away.

"No," Horcoff told the Canadian Press in their May story. "Never does."

Prior to the start of the next season, Pronger requested a trade and was moved to the Ducks. With the Oilers out of contention well before the playoffs, the club would also trade fan favourite Ryan Smyth to the New York Islanders at the deadline.

Edmonton would not make the playoffs again until the 2016-17 season when new captain McDavid would lead the club to its first playoff berth in 11 seasons.

With McDavid and Draisaitl under contract together for at least another two seasons, the Oilers will continue to be a Stanley Cup contender and is arguably the franchise best positioned to bring the Cup back to Canada.

Calgary Flames - Last Stanley Cup: 1989

Best playoff appearance since last Stanley Cup: 2003-04 Stanley Cup Final - Lost to Tampa Bay Lightning (4-3)

Calgary FlamesThe Flames went through a stretch of poor playoff performances after winning the franchise’s first and only Stanley Cup in 1988-89, as they failed to qualify or make it past the first round of the playoffs for 14 consecutive seasons. 

The Flames ended a seven-year playoff drought in 2003-04 thanks to Jarome Iginla, who tied for the league lead with 41 goals, and goaltender Miikka Kiprusoff, who posted an NHL-best 1.69 GAA along with a .933 save percentage after he was acquired via trade in Nov. 2003.

Calgary would enter the playoffs as the No. 6 seed and go on to upset the Vancouver Canucks. Presidents’ Trophy-winning Red Wings, and Kiprusoff’s former team, the Sharks, en route to the Cup Final against the Lightning, the first finals appearance by a Canadian team since the 1994 Vancouver Canucks.

In a series that became known for controversy, the Flames took a 3-2 series lead into Game 6 with a chance to win the Cup at home. Late in the third period with the score tied, the puck ricocheted off the skate of Flames forward Martin Gelinas and appeared to be stopped by Lightning goaltender Nikolai Khabibulin. Replays later indicated that the puck may have crossed the line, but the play was not reviewed, and the NHL would later rule the video as inconclusive.  The Flames would go on to lose Game 6 in double overtime and lose the series in Game 7. 

Flames general manager Craig Conroy, who was an alternate captain on the 2004 team, saw the extra pressure of playing in a Canadian market as motivation.

"A rallying thing," Conroy told the Canadian Press for their May story. "I felt more excited because they were so excited."

The Flames appeared to be on the upswing in the 2021-22 season as they won the Pacific Division around a pair of stars in Johnny Gaudreau and Matthew Tkachuk. However, a five-game second-round elimination at the hands of the Oilers, and the departure of both players, changed the foundation of the club. 

The Flames struggled following the changes, missing the playoffs this past season. Conroy says he still believes in the Flames’ current core and looks forward to competing for playoffs moving forward.

“I’m ready to accept this next challenge and promise to our fans I’m going to do everything I can to bring another Stanley Cup here,” Conroy said as he was introduced as the team’s new GM last month. “I was shocked that we didn’t make it [this season] and that’s unacceptable. With the guys we have here, I think we can make the playoffs.”

Toronto Maple Leafs - Last Stanley Cup: 1967

Best playoff appearance since last Stanley Cup: 1992-93 Conference Final - Lost to Los Angeles Kings (4-3)

Doug Gilmour Maple LeafsThe Maple Leafs have not been back to the Stanley Cup Final since their last Cup win in 1967. At 55 years, it is the longest championship drought in the NHL, two years longer than the Buffalo Sabres and Vancouver Canucks, who have not won since entering the league in the 1970-71 season. 

The 1992-93 season looked promising for the club, as they set franchise records in wins (44) and points (99). The Leafs eliminated the Detroit Red Wings and St. Louis Blues in the playoffs, setting up a Conference Finals matchup with Gretzky and the Kings. 

The series is remembered for multiple controversies. First, in the form of a dangerous open-ice hit delivered from the Kings’ Marty McSorley to the Leafs’ Doug Gilmore that led to Toronto coach Pat Burns attempting to scale the bench to get at Los Angeles coach Barry Melrose.

The second is perhaps the most infamous non-call in the history of the NHL.  

With Toronto leading the series 3-2 and Game 6 in overtime, Gretzky clipped Gilmour in the face with a high-stick, but the infraction went uncalled by official Kerry Fraser. The Great One scored the game-winner moments later in overtime to even the series. The Kings would go on to win the series, with Gretzky netting a hat trick in the deciding game to eliminate the Leafs. 

The club would get no closer to ending its Stanley Cup drought over the next 30 years, reaching no further than the Conference Finals.

The Maple Leafs took a step forward in 2023, reaching the second round for the first time since 2004. However, the team is heading to uncertain times, as the team recently fired general manager Kyle Dubas, replacing him with former Flames GM Brad Treliving.  

The core of Auston Matthews, Mitch Marner, William Nylander, and Morgan Rielly has shown the talent to be a contender, but it remains to be seen if the roster can produce in the playoffs and end its famed Stanley Cup drought.

Ottawa Senators - Last Stanley Cup: N/A

Best playoff appearance since last Stanley Cup: 2006-07 Stanley Cup Final - Lost to Anaheim Ducks (4-1)

Ottawa SenatorsThe Senators made the playoffs for nine consecutive seasons from 1996-97 to 2005-06 but did not make it further than the Conference Finals. After losing defenseman Zdeno Chara and goaltender Dominik Hasek to free agency, the Sens leaned on the trio of Daniel Alfredsson, Jason Spezza, and Dany Heatley, who combined for 279 points in the 2006-07 season. 

After finishing as the No. 4 seed, the Sens would go on to defeat the Pittsburgh Penguins, New Jersey Devils, and Buffalo Sabres, all in five games, to give them their first-ever trip to the Stanley Cup Finals against the Anaheim Ducks. 

The Ducks were able to shut down Ottawa’s top line in the Final, holding them to a combined five goals and three assists as they beat the Senators in five games. Spezza and Heatley in particular struggled in the series, combining for just one goal and two assists. 

Defenceman Wade Redden, who was a part of the Senators' run to the Cup Final, said the team’s postseason run was special, and the atmosphere brought on by Canadian fans was like no other.

"A very special time," Redden told the Canadian Press in May. "You see some of the teams that have won … [the attention is] probably not in their face as much. But that's what makes it more special. It would be great to win a Cup.

"To win in a Canadian city would be the ultimate."

The Senators would go on to make the playoffs in six of the next 10 seasons, making it as far as the Conference Finals in 2016-17 but have not made the playoffs over the past six seasons.

The team appears poised to snap their playoff drought next season, as they made a 13-point jump in the standings in 2022-23 and finished just out of a wild-card spot. With youngsters Brady Tkachuk and Tim Stutzle expected to take another jump, the Senators could soon find themselves as playoff contenders once again.

Vancouver Canucks - Last Stanley Cup: N/A

Best playoff appearance since last Stanley Cup:  1993-94 Stanley Cup Final - Lost to New York Rangers (4-3), 2010-11 Stanley Cup Final - Lost to Boston Bruins (4-3)

Vancouver CanucksThe Canucks have never won a Stanley Cup but have come excruciatingly close on a pair of occasions. Led by Pavel Bure’s 60 goals, the Canucks reached the Cup Final in the 1993-94 season, where they took on Mark Messier and the Presidents’ Trophy-winning New York Rangers.  

After going down 3-1 in the series, the Canucks battled back to force a deciding seventh game. However, the Rangers were able to earn the 3–2 victory, keeping Vancouver from winning their first Stanley Cup. 

Defenceman Dave Babych, a member of the 1994 Canucks team, told the Canadian Press this past May that the experience of going to the Final in a Canadian market left an impression on him, but admits that the loss still stings and that he still hasn’t watched a replay of the game. 

"It left an impression. If we'd have won, maybe we'd have to get security. That generation or two of people that went through that with us. Crazy,” Babych said. “Probably never [watch]. "Really have no use for it. [It] still hurts."

The Canucks would win the Presidents’ Trophy in 2010-11 en route to the franchise's second Stanley Cup Final appearance. The result would be the same as 1994, as the Bruins would come back from a 3-2 series deficit to win Game 7 and capture their first Stanley Cup in 39 years. The Canucks became the first Presidents’ Trophy winners since the 1995 Detroit Red Wings to lose in the Final. Vancouver’s 54 wins were also the most by a team that lost the Stanley Cup Final since the 1985 Philadelphia Flyers. 

Canucks forward Jannik Hansen also told the Canadian Press in May that the memory of the Game 7 loss has stuck with him over the past 12 years.

"Get reminded of it all time," he said. "If we'd won, I'd have a ring right now. You're immortalized. You're a champion until you die. It's one of those things that you carry with you until the end. It will be bitter every single time the playoffs roll around and the final comes and somebody lifts the Cup. That could have been us.” 

The Canucks are currently in a rebuilding phase around offensive superstar Elias Pettersson and defenceman Quinn Hughes but have missed the playoffs in seven of the past eight seasons.

Winnipeg Jets - Last Stanley Cup: N/A

Best Playoff Appearance since last Stanley Cup: 2017-18 Conference Finals - Lost to Vegas Golden Knights (4-1)

Winnipeg Jets Blake Wheeler Mark ScheifeleThe Winnipeg Jets are the only Canadian team that has never reached a Stanley Cup Final. The original iteration of the club, led by Dale Hawerchuk, made it as far as the second round in the 1984-85 and 86-87 seasons but were swept by Gretzky and the Oilers in the Division Finals in both seasons.

The club’s newest incarnation found some playoff success after relocating from Atlanta, beating the Minnesota Wild and Nashville Predators en route to the franchise’s first Conference Final appearance in 2017-18. The team, which finished with 114 points in the regular season, would fall to the Vegas Golden Knights in five games. 

However, the Jets have made it back to the second round just once in the five seasons since, including a first-round elimination at the hands of the Golden Knights this past season, and have won just three playoff series in 12 seasons.

Franchise cornerstones Mark Scheifele, Blake Wheeler, and Connor Hellebuyck are set to become unrestricted free agents in 2024. Pending restricted free agent Pierre-Luc Dubois is coming off a one-year deal and could sign another one-year contract to take him to UFA status.

With the club possibly teetering on the edge of a rebuild, combined with apparent friction in the locker room following head coach Rick Bowness’ post-elimination comments, general manager Kevin Cheveldayoff says the team has not yet made a decision on its future direction but says he was proud of the team’s performance as they continue to push for the franchise’s first Stanley Cup win.

“I firmly believed that we had what it took to be a playoff team and I’m proud of the group that they battled through that gauntlet and got to the point of making the playoffs,” Cheveldayoff said at his end-of-season availability in April. 

“There are contracts that we have to address. We'll go through the process and we'll make those proper decisions."

Files from The Canadian Press were used for this feature.