The 1989 Finals featured two coaches making their first appearances, as Calgary's Terry Crisp faced Montreal's Pat Burns.

Following the series, Bob Gainey, Rick Green, and Lanny McDonald retired, while long time defenceman Larry Robinson signed with the Los Angeles Kings, where he played the final three years of his career.

Calgary defeated the Vancouver Canucks 4–3, the Los Angeles Kings 4–0 and the Chicago Blackhawks 4–1 to advance to the Final.

In addition, the Flames path through the playoffs was made easier since their nemesis and reigning two-time defending cup champion, Edmonton Oilers, who had swept the Flames from the playoffs the previous year were eliminated by the Los Angeles Kings in the opening round.

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.

This was the first Cup Finals since 1984 that the CBC had the sole English-language rights to the entire series in Canada instead of having to share it with another network.

The 1989 Stanley Cup Finals was the first to feature a special commemorative patch on both teams' sweaters, in honor of the championship series.