When was the last time the Canadiens won the Stanley Cup?

New York Islanders head coach Patrick Roy was the starting goalie the last time the Canadiens won the Stanley Cup.
Canadiens goaltender Patrick Roy
Canadiens goaltender Patrick Roy / Focus On Sport/GettyImages

The Montreal Canadiens are the most successful franchise in NHL history. The Canadiens have 24 Stanley Cups in their trophy case, but they are part of one of the most surprising draughts in sports, as it's been 30 years since a Canadian team has won the historic trophy. It's fitting that the last Canadian team to win was the Montreal Canadiens. The Canadiens last won the Stanley Cup in 1993.

The Regular Season

Some younger hockey fans have no idea how dominant the Canadiens were in the 20th century. Entering the 1992-93 season, the Canadiens hadn't won a Stanley Cup in six seasons, their longest drought since 1944.

Jacques Demers took over the Canadiens in 1992 after Pat Burns left to coach the rival Toronto Maple Leafs. The Canadiens also made personnel changes, acquiring Vincent Damphousse and Brian Bellows.

Montreal dominated the regular season, sitting first overall until early March. However, they ended the season with three wins in their last 18 games, which included some of the worst play of Patrick Roy's Hall of Fame career.

The First Round

The Canadiens finished third in the Adams Division, forcing them to face arch-rival Quebec in the first round. It wasn't easy, as Roy continued his struggles and the Nordiques took a 2-0 series lead.

The Canadiens and Nordiques went into overtime in Game 3, and off-season acquisition became a hero in the Montreal Forum, scoring the winning goal 10:30 into the period. The Canadiens continued the momentum in Game 4, tying the series with a 3-2 win.

The Canadiens were up 1-0 in the second period when Patrick Roy took a shot off his collarbone. He allowed a goal shortly after, leaving the game with the injury. The Canadiens managed to keep the game tied at three going into the third period, and they were surprised by the return of Roy. Another overtime game was in the cards, as Damphousse contributed to the winner again, making the pass to Kirk Muller for the victory.

There was no turning back for the Avalanche, as they returned to Montreal for Game 6 and won 6-2.

The Second Round

The Canadiens had the luxury of facing the Buffalo Sabres in Round 2. The Sabres had finished well behind Adams Division-leading Boston but upset them with a four-game sweep.

The Canadiens took Games 1 and 2, with two 4-3 victories. The second win came in another overtime, with Guy Carbonneau scoring the winner.

The series moved to Buffalo but nothing else changed, as the Canadiens took another 4-3 win. Game 4 was expected to be a blowout for the Canadiens, as the Sabres lost Alex Mogilny and Pat LaFontaine to injuries, but the Sabres came back from 3-1 down to send the game to another overtime. This time, Kirk Muller was the hero, sweeping the Sabres and advancing to the conference finals.

The Third Round

The Canadiens got more luck in the third round, as they were on a collision course to take on the back-to-back champion Pittsburgh Penguins. The New York Islanders were without leading scorer Pierre Turgeon and finished 32 points behind Pittsburgh in the regular season.

The Islanders stretched that series to seven games, and took the win in overtime, making the Canadiens' path alot clearer.

The Canadiens won the first two games at the Forum once again, taking a 4-1 victory in Game 1, then winning 4-3 in double overtime in Game 2. Patrick Roy was finally rounding into form, and led his team to overtime, allowing just one goal. Unsurprisingly, the Canadiens came through again for their seventh-straight overtime win.

The Islanders made the series respectable with a win in Game 4, but the Canadiens took care of business in Game 5, advancing to the Stanley Cup Final.

Stanley Cup Final

The Canadiens had a bad finals matchup, facing the Los Angeles Kings and Wayne Gretzky. The Kings showed they weren't going out easy, taking the first game 4-1.

The Canadiens decided as a team for Guy Carbonneau to take the assignment of shadowing Gretzky for Game 2, and it proved to be their second best move of the season.

Their best move of the season came in Game 2 when Jacques Demers asked for a measurement on Marty McSorley's stick. It proved illegal, putting the Canadiens on a late powerplay while in a 2-1 deficit. The Canadiens tied the game, sending it into overtime, where they would win again on a hat trick by Eric Desjardins.

The Canadiens blitzed the Kings on the road in Game 3, getting out to a 3-0 lead, but blew the lead and forced another overtime. However, they ended the game quick, winning on a John LeClair wrap-around.

Patrick Roy began taking over the series in Game 4, getting the team into another overtime game, and once again, Leclair scored to make the series 3-1.

The Canadiens controlled the play in Game 5, getting out to a 4-1 lead in the third period, claiming their 24th Stanley Cup.

The country of Canada awaits another Stanley Cup, and their only hope now is the winner of the Edmonton Oilers-Vancouver Canucks series. The question all Canadiens fans want to know is when will it be the Habs turn to win their 25th?