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 (Oilers x 4, Canadiens x 1). This was the only time between 1980 and 1988 that neither the Oilers nor the New York Islanders won the Stanley Cup. It was the first Montreal-Calgary Final since 1924, when the Canadiens defeated the Calgary Tigers. The Canadiens and Flames would get a rematch in 1989, with Calgary winning in six games.
The 1985–86 Montreal Canadiens season was the team's 77th season. The team won the Stanley Cup for the first time in seven seasons, and their 23rd overall.