1989 Stanley Cup playoffs

This was the final year that all of the Division Semifinals began with teams playing the first four games in a span of five days.

The playoffs concluded on May 25 with the champion Calgary Flames defeating the Montreal Canadiens 4–2 to win the Stanley Cup Finals four games to two.

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 NHL game.

Flames co-owner Sonia Scurfield became the first Canadian woman to have her name inscribed on the Stanley Cup.

Wayne Gretzky and the Los Angeles Kings met the defending champion Oilers in the first round.

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' unpenalized hit on Flyers forward Brian Propp in game one.

Former Flyers head coach Mike Keenan led Chicago to the Campbell Conference finals in his first year behind the bench.

Montreal won all three previous meetings, including last year's Adams Division Semifinals in six games.

Boston won all three previous meetings, including last year's Adams Division Semifinals in six games.

Washington won both prior meetings, including last year's Patrick Division Semifinals in seven games.

The best of these chances was a breakaway for Canucks' captain Stan Smyl who was stopped by Calgary goaltender Mike Vernon.

Edmonton won two of the past three playoff series, including the most recent in the 1987 Smythe Division Semifinals in five games.

This was the second consecutive and fourth overall playoff meeting between these two teams; with Los Angeles winning two of the three previous series.

This was the second playoff series between these two teams, with the only previous meeting being the 1986 Stanley Cup Finals where Montreal defeated Calgary in five games.

Doug Gilmour scored two goals in the third period, including the eventual game and Cup winner to cement their first title for the Flames.