Yes. It has happened.
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 Montreal Canadiens and the Calgary Flames.
The Detroit Red Wings defeated the Washington Capitals, 4 games to 0, to win the Stanley Cup in 1998.
the big prize in Canadian football, is called the Grey Cup.
Montreal Canadiens - 4 vs Chicago Blackhawks - 3
Montréal AAA and the Victoria Victorians (First 2 team in the Stanley Cup final)
Canadian Governor General Stanley donated the Stanley cup the nhl
Detroit red wings
this used to be possible, but now the Stanley Cup Finals are between an eastern conference team and a western conference team
A team can win the Stanley Cup by competing in the National Hockey League (NHL) playoffs and winning four rounds of best-of-seven series against other teams. The team that wins the final series is awarded the Stanley Cup.
27 different teams
Toronto has won more Stanley Cups, having won 13 Stanley Cups.The original Ottawa Senators have won the Stanley Cup 5 times, but the current Ottawa Senators have not yet won the Stanley cup.