Long considered Canada’s national sport, young fans across the country proudly wear their favourite team’s jersey while playing road hockey while older ones can be found sitting at their favourite watering hole, watching ‘their team’ play or passionately debating among friends who the greatest player of all time is—or who’s most likely to win the next Stanley Cup.
Hockey plays a significant role in shaping our Canadian identity. The team which has captivated fans across Canada for decades is the Montreal Canadiens. They are the most successful Canadian team, having won 24 Stanley Cups.
Following closely behind the Habs are their rivals, the Toronto Maple Leafs, who have won 13 Stanley Cups. While out west, the Edmonton Oilers have celebrated five Stanley Cup triumphs, and their Alberta rivals, the Calgary Flames, have hoisted the Stanley Cup once in franchise history.
Staying out west, the Vancouver Canucks have made it to the Stanley Cup finals twice, while the Winnipeg Jets have had some great teams over the years but have yet to experience playoff success.
Meanwhile, in the nation’s capital, the Ottawa Senators, since coming back to the NHL in 1992, have come close but have yet to hoist their first Stanley Cup.
Back in the spring of 1993, Canadian hockey fans had reason to feel strong pride as the Montreal Canadiens, led by solid goaltending from future Hockey Hall of Famer Patrick Roy, completed a successful playoff journey on June 9, defeating the Los Angeles Kings to win their record-setting 24th Stanley Cup.
What’s shocking is that no Canadian team has captured the Stanley Cup since that night.
Various Canadian teams, including the Senators, Oilers, Canadiens, and Canucks, have since made it to the finals, and in some cases, come within a game of bringing the Cup back to Canada—but the drought continues.
It’s been an ugly 32 years.
A year after The Habs won the Cup in ’93, another Canadian team came close. The Canucks thrilled their West Coast fans when they embarked on a captivating playoff run, culminating in an epic 1994 Stanley Cup Finals series that continues to be talked about today—a heartbreaking Game 7 loss to the New York Rangers.
In 2011, after coming off a solid 117-point campaign and winning the Presidents’ Trophy, Vancouver made it to the Stanley Cup Finals, where they once again lost Game 7, this time to the Boston Bruins. It was especially painful for Canuck fans who watched as Vancouver jumped out to a 2-0 and 3-2 series lead but couldn’t close things out.
In 2024, the talented Oilers experienced Game 7 heartbreak. The team overcame a 3-0 Stanley Cup Finals series deficit to force a winner-takes-all decisive Game 7, only to come up short against the Panthers.
The Oilers were on a mission this year to win the Cup, but found themselves competing once again in the finals against the defending champions, the Panthers. With all of Canada closely following this rematch of a year ago, the Oilers, who have superstars in Connor McDavid and Leon Draisaitl, to name a few, came up short, losing in 6 games.
Oilers fans are no strangers to Game 7 heartbreak, having also experienced that painful emotion in 2006 when their team lost the decisive Stanley Cup Finals winner-take-all game against the Carolina Hurricanes.
Besides the Oilers and Canucks, three other Canadian teams—the Canadiens, Flames, and Senators—have advanced to the Stanley Cup Finals over the past 32 years. During the 2021 COVID season, Montreal shocked the hockey world when, after finishing fourth in the North Division, they caught fire in the postseason and made it to the Stanley Cup Finals, where they fell short, losing in Game 5 against the Tampa Bay Lightning.
In the early 2000s, both Ottawa and Calgary had opportunities to end Canada’s Stanley Cup drought, but couldn’t quite do it. Back then, the Senators were stacked with talented players such as Dany Heatley, Jason Spezza, Daniel Alfredsson and exceptional goaltending from the late Ray Emery.
In 2007, following a memorable 105-point season which saw them finish second in the Northeast Division, Ottawa went on to defeat the Pittsburgh Penguins, New Jersey Devils and Buffalo Sabres before falling short in the Stanley Cup Finals against the Anaheim Ducks.
Three years earlier it was the Flames who captured Canada’s attention when led by a core of young talented players such as future Hockey Hall of Famer Jarome Iginla along with defenceman Robyn Regehr and goalie Miikka Kiprusoff, they had great playoff success as they defeated the Canucks, Red Wings, and San San Jose Sharks before falling just short in the 2007 Stanley Cup Finals.
It’s only a matter of time before a Canadian team snaps that 32-year drought and wins the Stanley Cup.
The Jets are the defending Presidents’ Trophy winners and have the league’s best goalie in Connor Hellebuyck, while the Oilers have not only McDavid and Draisaitl in their primes but also Zach Hyman (who was injured in the 2025 finals), Ryan Nugent-Hopkins and defenceman Evan Bouchard.
Another Canadian team that, on paper, should be a Stanley Cup contender is the Maple Leafs. The team boasts star power in Auston Matthews, William Nylander, Matthew Knies, and defenceman Morgan Rielly, to name a few.
Only time will tell if the Stanley Cup ends its 32-year vacation from Canada—or if we’re headed for year 33 of polite disappointment.
Photo: Courtesy USA Today
