The Montreal Canadiens who have won the Stanley Cup 24 times!
55. Most of them were during the early Challenge Cup years, when the Cup was to be awarded to "the best amateur hockey team in Canada", as Lord Stanley originally intended. The last two Canadian teams to play for the Cup were the Calgary Flames and Montreal Canadiens in 1989. Calgary won in 6 games.
The Toronto Maple Leafs have lost in the Stanley Cup Finals 8 times. Both the Montreal Canadiens and the Philadelphia Flyers have lost 6 times.
Howe has won the Stanley Cup for 4 times: 1950, 1952, 1954 and 1955. All with the Detroit Red Wings.
The New York Islanders won 4 straight Stanley Cups (1980-1983). In 1984, they went back to the Stanley Cup Finals for the 5th straight time but ultimately lost to the Edmonton Oilers in 5 games. The Oilers had lost the Stanley Cup Finals to the Islanders in 1983.
The Calgary Flames have won the Stanley Cup only once in franchise history. They won it in 1989. Some players on the winning team were Al MacInnis, Mike Vernon, Lanny Mcdonald, and Doug Gilmour.
11 times
The Montreal Canadiens who have won the Stanley Cup 24 times!
The St. Louis Blues have been to the Stanley Cup Finals three times, 1968, 1969 and 1970.
They have been to the Stanley Cup finals 4 times and countless playoffs.
55. Most of them were during the early Challenge Cup years, when the Cup was to be awarded to "the best amateur hockey team in Canada", as Lord Stanley originally intended. The last two Canadian teams to play for the Cup were the Calgary Flames and Montreal Canadiens in 1989. Calgary won in 6 games.
19 times in the finals.
Six appearances in the finals as of 2017.
The Calgary Flames have won the Stanley Cup once, in 1989 versus the Montreal Canadiens.They Calgary Flames finished top in the league during the regular season. The Flames beat the Canucks in the first round, then proceeded to sweep the Los Angeles Kings in the second round. In the third round they overcame Chicago Blackhawks in 5 games to make it to the final and fourth round. The Calgary Flames defeated the Montreal Canadiens in a best of 7 series by winning 4 of 6 games. Terry Crisp was coach.
Six appearances in the finals as of 2017.
ONCE
Three so far.