The 1986 Stanley Cup Final NHL championship series was contested by the Calgary Flames in their first Final appearance and the Montreal Canadiens in their 32nd. The Canadiens would win the best-of-seven series four games to one, to win their twenty-third Stanley Cup, and their seventeenth in their last eighteen Finals appearances dating back to 1956.

It was the first all-Canadian finals since Montreal lost to the Toronto Maple Leafs in 1967, the last year of the Original Six era. This would be the fourth of eight consecutive Finals contested by a team from Alberta (the Edmonton Oilers appeared in six, the Flames in two), and the third of five consecutive Finals to end with the Cup presentation on Alberta ice (the Oilers won four, the Canadiens one). This was the only time between 1980 and 1988 that neither the Oilers nor the New York Islanders won the Stanley Cup.

Although this was the first ever postseason meeting between the two teams, it was not the first Montreal-Calgary Final. The first Final between teams from Montreal and Calgary took place in 1924 when the Canadiens defeated the Western Canada Hockey League champion Calgary Tigers. The Canadiens and Flames would get a rematch in 1989, with Calgary winning in six games.

Calgary defeated the Winnipeg Jets 3–0, the defending champion and in-province rival Edmonton Oilers 4–3, and the St. Louis Blues 4–3 to advance to the final.

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