1989 Stanley Cup playoffs The 1989 Stanley Cup playoffs , the championship of the National Hockey League ( NHL ) began on April 5 , after the conclusion of the 1988 – 89 NHL season . The playoffs concluded on May 25 with the champion Calgary Flames defeating the Montreal Canadiens 4 – 2 to win the Stanley Cup Final series four games to two . Series . The 1989 Stanley Cup playoffs featured two Canadian hockey teams , the Montreal Canadiens and the Calgary Flames . Montreal finished the regular season with 115 points , only two behind the league leader Calgary . They had last faced each other only three years earlier , with Montreal winning a five - game series in 1986 . Calgary was only the second opposing team in NHL history to win a Stanley Cup at the Montreal Forum ( the New York Rangers defeated the Montreal Maroons in 1928 ) and the first to do so against the Canadiens . Flames defenceman Al MacInnis won the Conn Smythe Trophy as playoff MVP , while Lanny McDonald , who ended the regular season with exactly 500 goals , got his name on the Cup in his last ever NHL game . Flames co - owner Sonia Scurfield became the first Canadian woman to have her name inscribed on the Stanley Cup . On their way to the Finals , Montreal lost only three games while eliminating the Hartford Whalers , Boston Bruins , and Philadelphia Flyers . Calgary survived a seven - game series with the Vancouver Canucks before sweeping the Los Angeles Kings and eliminating the surprising Chicago Blackhawks in five to reach the Cup Finals . One of the interesting stories of these playoffs , though , was Gretzky and the Los Angeles Kings meeting the defending champion Oilers in the first round . The previous season saw the mighty Edmonton Oilers sweep the Boston Bruins in the Stanley Cup finals as Gretzky earned the Conn Smythe Trophy setting playoff records for playoff assists , assists in a finals series and points in a finals series . On August 9 , 1988 , the Oilers traded Gretzky to the Kings . The Gretzky - led Kings and Oilers ( with many veteran super - stars ) met in the first round of the Smythe Division playoffs , which made for an exciting " return " of Gretzky to Edmonton . In a tough seven game series , Gretzky and the Kings took down the defending Stanley Cup champions after falling behind 3 games to 1 . In the second round Gretzky and the Kings were no match for the eventual champion Calgary Flames , who swept them in 4 games . Events of note in the postseason , were that Philadelphia Flyers goaltender Ron Hextall became the first netminder to shoot and score a goal in the playoffs , a shorthanded , empty - net score in Game 5 of the Patrick Division Semifinal against the Washington Capitals . One round later , Mario Lemieux torched the Flyers for an NHL - record five goals and eight points in a 10 – 7 Pittsburgh win in Game 5 of the Patrick Division Finals . Hextall then made headlines in the Wales Conference Finals , attacking Montreal ' s Chris Chelios in the late stages of Game 6 as retribution for Chelios ' brutal and unpenalized hit on Flyers forward Brian Propp in Game 1 . Hextall received a 12 - game suspension at the start of the 1989 – 90 NHL season for his actions . Also , former Flyers head coach Mike Keenan led Chicago to the Campbell Conference Finals in his first year behind the bench . The Hawks , with 66 points , had the fewest points of any playoff team that season ( and tied in the overall standings with New Jersey , a fifth - place team in the Patrick Division ) , yet played a fiercely energetic and defensive game which saw them upset first - place Detroit and then St . Louis before bowing to Calgary . Division semi - finals . Hartford Whalers vs . Montreal Canadiens " Montreal wins best - of - seven series 4 games to 0 " Buffalo Sabres vs . Boston Bruins " Boston wins best - of - seven series 4 games to 1 " Washington Capitals vs . Philadelphia Flyers " Philadelphia wins best - of - seven series 4 games to 2 " New York Rangers vs . Pittsburgh Penguins " Pittsburgh wins best - of - seven series 4 games to 0 " Chicago Blackhawks vs . Detroit Red Wings " Chicago wins best - of - seven series 4 games to 2 " Minnesota North Stars vs . St . Louis Blues " St . Louis wins best - of - seven series 4 games to 1 " Vancouver Canucks vs . Calgary Flames Coming into this series , many people expected that the mighty Flames would defeat the Canucks in 4 or 5 games , due to Calgary having a 43 point edge in the regular season . Instead , Vancouver would take Calgary to a thrilling seven game classic . The seventh game would go into overtime , both teams having great chances , the best being a breakaway chance for Vancouver Canuck ' s captain Stan Smyl , only for Mike Vernon to make the unbelievable save . However , Vancouver couldn ' t pull off the upset , as Joel Otto scored the winner ( via a deflection from his skate ) with : 39 seconds left in the first overtime to send the Calgary Flames into the Smythe Division Final . " Calgary wins best - of - seven series 4 games to 3 " Edmonton Oilers vs . Los Angeles Kings " Los Angeles wins best - of - seven series 4 games to 3 " Division finals . Boston Bruins vs . Montreal Canadiens " Montreal wins best - of - seven series 4 games to 1 " Philadelphia Flyers vs . Pittsburgh Penguins " Philadelphia wins best - of - seven series 4 games to 3 " Chicago Blackhawks vs . St . Louis Blues " Chicago wins best - of - seven series 4 games to 1 " Los Angeles Kings vs . Calgary Flames " Calgary wins best - of - seven series 4 games to 0 " Conference finals . Philadelphia Flyers vs . Montreal Canadiens " Montreal wins best - of - seven series 4 games to 2 " Chicago Blackhawks vs . Calgary Flames " Calgary wins best - of - seven series 4 games to 1 " Final . Montreal Canadiens vs . Calgary Flames The Stanley Cup Final was decided between the top two teams of the 1988 – 89 NHL regular season . Captain Lanny McDonald scored the second Flames goal in game six . This turned out to be the last goal in his NHL Hall of Fame career because he retired during the following off - season . Doug Gilmour scored two goals in the third period , including the eventual game and Cup winner to cement the victory for the Flames . " Calgary wins best - of - seven series 4 games to 2 " Player statistics . Playoff scoring leaders . " Note : GP = Games played ; G = Goals ; A = Assists ; Pts = Points "