PITTSBURGH, PA – MAY 15: Brian Bellows #23 of the Minnesota North Stars skates on the ice against the Pittsburgh Penguins during Game 1 of the 1991 Stanley Cup Finals on May 15, 1991, at the Kane won the Stanley Cup three times with Chicago (2010, 2013, 2015) and is third in team history in points in the Stanley Cup Playoffs with 132 (52 goals, 80 assists) in 136 games. In 18 seasons, Ovechkin has won three Hart Trophies, awarded to the league’s most valuable player, and in the 2017-18 season he lifted the Capitals’ only Stanley Cup. Montreal won Lord Stanley’s Cup four more times in the 60′s and then six times in the 70′s including going back-to-back-to-back-to-back from 1976 to 1979. Since then the Canadiens have gone 1. He Never Won a Stanley Cup After Being Traded From Edmonton. My earliest recollections of hockey as a youngster begin when Gretzky was just winding down his time in Edmonton, winning his final of 4 Stanley Cup championships with the Oilers in 1988 before shockingly being dealt to the Los Angeles Kings later that summer. Welcome to NHL 99, The Athletic ’s countdown of the best 100 players in modern NHL history. We’re ranking 100 players but calling it 99 because we all know who’s No. 1 — it’s the 99 What team has won the most Stanley Cups? The Canadiens have won the most Cups with 24. However, it's been 30 years since the last time Montreal hoisted the trophy, which came in 1993. And while the presence of Wayne Gretzky and his running mates may have been intimidating, Montreal held firm. After dropping Game 1, the Habs rattled off four victories to claim the title. The Stanley Cup had returned to Canada; little did anyone know that it wouldn’t be back for decades. Historically, Canadian teams have won plenty of .

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