1986 Stanley Cup playoffs The 1986 Stanley Cup playoffs , the championship of the National Hockey League ( NHL ) began on April 9 , after the conclusion of the 1985 – 86 NHL season . The playoffs concluded on May 24 with the champion Montreal Canadiens defeating the Calgary Flames 4 – 3 to win the series four games to one and win the Stanley Cup . Series . The playoffs of 1986 saw three first place teams eliminated in the opening round and the fourth , Edmonton , bowed out in the second . The Montreal Canadiens decided to go with a rookie goaltender by the name of Patrick Roy . This decision proved to be a good one just like when the Canadiens rode rookie goalie Ken Dryden to a Stanley Cup championship in 1971 . In the Final , the Canadiens beat the Calgary Flames , who were also riding a rookie netminder , Mike Vernon . Patrick Roy won the Conn Smythe Trophy as the playoff MVP and had a sparkling 1 . 92 goals against average along with 15 wins . Division semi - finals . Adams Division Semi - Finals . Hartford Whalers vs . Quebec Nordiques This was Hartford ' s lone playoff series victory in their NHL history prior to moving to Carolina . " Hartford wins best - of - five series 3 – 0 . " Boston Bruins vs . Montreal Canadiens " Montreal wins best - of - five series 3 – 0 . " Patrick Division Semi - Finals . New York Rangers vs . Philadelphia Flyers " New York Rangers wins best - of - five series 3 – 2 . " New York Islanders vs . Washington Capitals " Washington wins best - of - five series 3 – 0 . " Norris Division Semi - Finals . Toronto Maple Leafs vs . Chicago Black Hawks " Toronto wins best - of - five series 3 – 0 . " St . Louis Blues vs . Minnesota North Stars " St . Louis wins best - of - five series 3 – 2 . " Smythe Division Semi - Finals . Vancouver Canucks vs . Edmonton Oilers " Edmonton wins best - of - five series 3 – 0 . " Winnipeg Jets vs . Calgary Flames " Calgary wins best - of - five series 3 – 0 . " Divisional Finals . Hartford Whalers vs . Montreal Canadiens The upstart Whalers pushed the eventual Stanley Cup Champions to the limit before falling . Claude Lemieux scored the series - winning overtime goal for Montreal . " Montreal wins best - of - seven series 4 – 3 . " New York Rangers vs . Washington Capitals " New York Rangers wins best - of - seven series 4 – 2 . " Toronto Maple Leafs vs . St . Louis Blues " St . Louis wins best - of - seven series 4 – 3 . " Calgary Flames vs . Edmonton Oilers The deciding goal of game seven between the Oilers and Flames was scored five minutes into the third period when Edmonton ' s Steve Smith attempted a cross - ice pass from the side of his own net and the puck struck goaltender Grant Fuhr ' s leg and went in the Edmonton goal . This is significant because it eliminated the Oilers from the playoffs and prevented them from possibly winning a third straight Stanley Cup . The series was the Flames ' only playoff victory over the Oilers in the Battle of Alberta ( Edmonton beat Calgary in 4 other playoff series ) , but significantly fueled the rivalry between the teams . " Calgary wins best - of - seven series 4 – 3 " Conference Finals . New York Rangers vs . Montreal Canadiens This series is best remembered for the third game , in which the Rangers badly outshot the Habs , but were stymied by Patrick Roy . Another Montreal rookie , Claude Lemieux , scored in overtime — his second overtime goal of the playoffs . " Montreal wins best - of - seven series 4 – 1 " St . Louis Blues vs . Calgary Flames In Game 6 , the Flames led 4 – 1 after two periods and 5 – 2 early in the third , but the Blues came back to tie it and then won on an overtime goal by Doug Wickenheiser . In Game 7 , the Flames were up 2 – 0 before the Blues scored in the third to cut the lead in half . There wouldn ' t be another comeback , though , as Mike Vernon and the Flames withstood a late assault to advance to their first Stanley Cup Final . " Calgary wins best - of - seven series 4 – 3 " Stanley Cup Final . Montreal Canadiens vs . Calgary Flames " Montreal wins best - of - seven series 4 – 1 "