The 1989 Stanley Cup Final was between the Calgary Flames and the Montreal Canadiens, the top two teams during the 1988–89 NHL regular season. As of 2009, this is the most recent time that the first two seeds met in the Stanley Cup Final, as the New Jersey Devils had one win less than the Detroit Red Wings during the 2000-01 season when they played against the Colorado Avalanche in the 2001 finals. It is also the most recent time that the Final series was played entirely in Canada. The Calgary Flames are also the first relocated NHL team (from Atlanta in 1980-81) to win the Stanley Cup.
Calgary defeated the Vancouver Canucks 4–3, the Los Angeles Kings 4–0 and the Chicago Blackhawks 4–1 to advance to the Final. Montreal defeated the Hartford Whalers 4–0, the Boston Bruins 4–1 and the Philadelphia Flyers 4–2.
Co-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. Al MacInnis won the Conn Smythe Trophy as playoff MVP, and at 31 points, became the first defenceman to lead the NHL in post-season scoring. The Calgary Flames are the only visiting team to have won the Stanley Cup on the Canadiens' home ice.