Last time a Canadian team won the Stanley Cup: Oilers are four wins away from ending lengthy drought

It's been over three decades since a Canadian team lifted the Stanley Cup

By Austin Nivison

May 29, 2025 at 10:48 pm ET • 1 min read

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Canadian fans have exhibited quite a bit of patience waiting for the Stanley Cup to make its return north of the border. How much longer will they have to wait? Perhaps not long with the Edmonton Oilers in the Stanley Cup Final for the second consecutive season.

On June 9, 1993, the Montreal Canadiens passed around the Stanley Cup after beating the Los Angeles Kings in five games. "Jurassic Park" was mauling its competition at the box office. "Roseanne" and 'Home Improvement" were on just about every TV in America. Janet Jackson's "That's the Way Love Goes" was topping the billboard charts.

Since then, the Stanley Cup has taken up residence in the United States for 32 straight years.

Going into the Stanley Cup Final, just one Canadian team remains. After falling behind 2-0 in their first-round series against the Los Angeles Kings, the Oilers have gone 14-2 while taking down the Vegas Golden Knights and Dallas Stars in just five games.

Connor McDavid and Leon Draisaitl are at the height of their powers, and they lead the NHL in postseason scoring. The team defense has been impressive to watch, and Stuart Skinner has been dialed in between the pipes after losing the starting job earlier in the playoffs.

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Everything is clicking for Edmonton, but it will face a familiar and formidable foe in the Stanley Cup Final. The Florida Panthers defeated the Oilers in seven games to capture the Cup a year ago, and they might even be a little bit better this time around.

These last four wins will be the toughest for the Oilers, but they have all pieces to bring the Stanley Cup north of the border for the first time since 1993. Until then, here is every Canadian team's Stanley Cup drought.

Toronto Maple Leafs | 58 years

Stanley Cup wins: 13
Years won: 1967, 1964, 1963, 1962, 1951, 1949, 1948, 1947, 1945, 1942, 1932, 1922, 1918

Vancouver Canucks | 55 years

Stanley Cup wins: 0
Years won: N/A

Calgary Flames | 36 years

Stanley Cup wins: 1
Years won: 1989

Edmonton Oilers | 35 years

Stanley Cup wins: 5
Years won: 1990, 1988, 1987, 1985, 1984

Ottawa Senators | 33 years

Stanley Cup wins: 0
Years won: N/A

Montreal Canadiens | 32 years

Stanley Cup wins: 23
Years won: 1993, 1986, 1979, 1978, 1977, 1976, 1973, 1971, 1969, 1968, 1966, 1965, 1960, 1959, 1958, 1957, 1956, 1953, 1946, 1944, 1931, 1930, 1924, 1926