The Stanley Cup

Rookie goaltender Patrick Roy led the Canadiens to their 23rd Stanley Cup championship in 1986 over the Calgary Flames in the first all-Canadian Stanley Cup final since 1967.[122] The 1986 Canadiens were young and led by rookie head coach Jean Perron and forward Claude Lemieux,[123] in addition to Roy who became the youngest player in league history to win the Conn Smythe Trophy.[124] Brian Skrudland, another rookie, scored the game-winning goal just nine seconds into overtime of the second game of the finals – the fastest overtime goal in league history.[122] The two teams met again in the 1989 Stanley Cup Finals, the most recent all-Canadian Stanley Cup Final, with the Flames emerging victorious in six games. It was the only time a visiting team defeated the Canadiens to win the Cup on Forum ice.[125]

The Stanley Cup celebrated its 100th anniversary in 1993, returning again to Canada with the Canadiens' 24th Stanley Cup victory,[126] the most recent NHL championship won by a Canadian team.[127] After losing the first game of their Adams Division semi-final to the Quebec Nordiques in overtime, the Canadiens won ten overtime games en route to the title, setting an NHL record for most consecutive overtime victories in a playoff year.[128] As with the 1986 championship, the team was led by Roy, who won his second Conn Smythe Trophy.[126] The defining moment of the 1993 Stanley Cup Finals occurred in the second game, with less than two minutes to play and Montreal trailing the series 1–0 and the game 2–1. Attempting to gain an advantage for his team, coach Jacques Demers called for a measurement of Los Angeles Kings forward Marty McSorley's stick. Referee Kerry Fraser determined that the blade had an illegal curve, and assessed a penalty against McSorley. Montreal scored on the power play to tie the game, and then won in overtime 3–2, to tie the series.[129] Montreal also won games three and four in overtime before eliminating the Kings in game 5 by a 4–1 score.[130] The celebration was marred by one of the worst riots in Montreal history, as fans rioted through downtown Montreal causing over $2.5 million in property damage and 168 injuries.[131]



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