The 1986 Stanley Cup Finals was the championship series of the National Hockey League's (NHL) 1985–86 season, and the culmination of the 1986 Stanley Cup playoffs. It was contested between the Campbell Conference champion Calgary Flames and the Wales Conference champion Montreal Canadiens. The Canadiens won the best-of-seven series, four games to one, to win their 23rd Stanley Cup, and their 17th in their last 18 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 was the fifth of nine consecutive Finals contested by a team from Western Canada, the fourth of eight contested by a team from Alberta (the Edmonton Oilers appeared in six, the Flames in two, the Vancouver Canucks in one), 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 (four wins) nor the New York Islanders (four wins) won the Stanley Cup.

Although this was the first ever postseason meeting between the two teams, it was not the first Montreal-Calgary Finals. The first Finals 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 met again in a rematch in 1989, with Calgary winning in six games.

The format reverted to the 2-2-1-1-1 format that had been in use since the re-alignment which followed the 1981. The previous four Finals had used a 2-3-2 format, although only the latter two of those Finals lasted five 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.

Montreal defeated rival Boston Bruins 3–0, the Hartford Whalers 4–3, and the New York Rangers 4–1 to make it to the final.

Brian Skrudland's game-winning goal in game two ended the shortest overtime in NHL playoff history, at a mere nine seconds. Montreal rookie goaltender Patrick Roy was awarded the Conn Smythe Trophy as the playoff MVP.

Years indicated in boldface under the "Finals appearance" column signify that the player won the Stanley Cup in the given year.

Calgary Flames

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#	Nat	Player	Position	Hand	Acquired	Place of birth	Finals appearance
15		Robin Bartel	D	L	1985–86	Drake, Saskatchewan	first
4		Paul Baxter	D	R	1983–84	Winnipeg, Manitoba	first
21		Perry Berezan	C	R	1983	Edmonton, Alberta	first
26		Steve Bozek	LW	L	1983–84	Kelowna, British Columbia	first
14		Brian Bradley	C	R	1983	Kitchener, Ontario	first
25		Yves Courteau	RW	R	1982–83	Montreal	first
17		Mike Eaves	C	R	1983–84	Denver, Colorado	first
22		Nick Fotiu	LW	L	1985–86	Staten Island, New York	second (1979)
16		Brett Hull	RW	R	1984	Belleville, Ontario	first
19		Tim Hunter	RW	R	1979	Calgary, Alberta	first
6		Terry Johnson	D	L	1985–86	Calgary, Alberta	first
31		Rejean Lemelin	G	L	1978–79	Quebec City, Quebec	first
12		Hakan Loob	RW	R	1980	Visby, Sweden	first
2		Al MacInnis	D	R	1981	Inverness, Nova Scotia	first
34		Jamie Macoun	D	L	1982–83	Newmarket, Ontario	first
9		Lanny McDonald – C	RW	R	1981–82	Hanna, Alberta	first
7		Joe Mullen	RW	R	1985–86	New York	first
29		Joel Otto	C	R	1984–85	Elk River, Minnesota	first
11		Colin Patterson	LW	R	1983–84	Rexdale, Ontario	first
24		Jim Peplinski – C	RW	R	1979	Renfrew, Ontario	first
10		Dan Quinn	C	L	1983	Ottawa, Ontario	first
23		Paul Reinhart	D	L	1979	Kitchener, Ontario	first
8		Doug Risebrough – C	C	L	1982–83	Guelph, Ontario	fifth (1976, 1977, 1978, 1979)
10		Gary Roberts	LW	L	1984	North York, Ontario	first
5		Neil Sheehy	D	R	1983–84	Fort Frances, Ontario	first
20		Gary Suter	D	L	1984	Madison, Wisconsin	first
27		John Tonelli	LW	L	1985–86	Hamilton, Ontario	sixth (1980, 1981, 1982, 1983, 1984)
30		Mike Vernon	G	L	1981	Calgary, Alberta	first
33		Carey Wilson	C	R	1983–84	Winnipeg, Manitoba	first

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Montreal Canadiens

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#	Nat	Player	Position	Hand	Acquired	Place of birth	Finals appearance
12		Serge Boisvert	RW	R	1984–85	Drummondville, Quebec	first
21		Guy Carbonneau	C	R	1979	Sept-Îles, Quebec	first
24		Chris Chelios	D	R	1981	Chicago	first
20		Kjell Dahlin	RW	L	1981	Timrå, Sweden	first
27		Lucien DeBlois	RW	R	1984–85	Joliette, Quebec	second (1979)
23		Bob Gainey – C	LW	L	1973	Peterborough, Ontario	fifth (1976, 1977, 1978, 1979)
29		Gaston Gingras	D	L	1979	Témiscaming, Quebec	first
5		Rick Green	D	L	1982–83	Belleville, Ontario	first
31		John Kordic	RW	R	1983	Edmonton, Alberta	first
18		Tom Kurvers	D	L	1981	Minneapolis, Minnesota	first
38		Mike Lalor	D	L	1985–86	Buffalo, New York	first
32		Claude Lemieux	RW	R	1983	Buckingham, Quebec	first
17		Craig Ludwig	D	L	1980	Rhinelander, Wisconsin	first
8		David Maley	LW	L	1982	Beaver Dam, Wisconsin	first
35		Mike McPhee	LW	L	1980	Sydney, Nova Scotia	first
26		Mats Naslund – A	LW	L	1979	Timrå, Sweden	first
30		Chris Nilan	RW	R	1978	Boston, Massachusetts	first
44		Stephane Richer	RW	R	1984	Ripon, Quebec	first
19		Larry Robinson – A	D	L	1971	Winchester, Ontario	sixth (1973, 1976, 1977, 1978, 1979)
28		Steve Rooney	LW	L	1981	Canton, Massachusetts	first
33		Patrick Roy	G	L	1984	Quebec City, Quebec	first
39		Brian Skrudland	C	L	1985–86	Peace River, Alberta	first
15		Bobby Smith	C	L	1983–84	North Sydney, Nova Scotia	second (1981)
1		Doug Soetaert	G	L	1984–85	Edmonton, Alberta	first
25		Petr Svoboda	D	L	1984	Most, Czechoslovakia	first
14		Mario Tremblay – A	RW	R	1974	Alma, Quebec	fifth (1976, 1977, 1978, 1979)
11		Ryan Walter	LW	L	1982–83	New Westminster, British Columbia	first

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The 1986 Stanley Cup was presented to Canadiens captain Bob Gainey by NHL President John Ziegler following the Canadiens 4–3 win over the Flames in game five.

The following Canadiens players and staff had their names engraved on the Stanley Cup

1985–86 Montreal Canadiens

Some 5,000 jubilant Montreal fans celebrating the Canadiens' Stanley Cup win over the Calgary Flames rampaged through the city's downtown, causing over CA$1 million worth of damage.^[1]

In Canada, this was the second and final year that the English-language rights of the Cup Finals were shared between CBC and CTV. For games one and two, CBC only had the rights to air them locally in Montreal and Calgary, while CTV broadcast them to the rest of the country. CBC then had the exclusive rights to televise games three, four, and five nationally. Had the series gone to a seventh game, then both CBC and CTV would have simultaneously televised it while using their separate production facilities and crews. After the season, CTV pulled the plug on their two-year-long venture with the NHL, and their rights package was eventually given to the Global-Canwest consortium.

This was the first of three consecutive seasons that ESPN televised the Stanley Cup Finals in the United States.

• List of Stanley Cup champions
• 1985–86 NHL season

• Diamond, Dan (2000). Total Stanley Cup. Toronto: Total Sports Canada. ISBN 978-1-892129-07-9.
• Podnieks, Andrew; Hockey Hall of Fame (2004). Lord Stanley's Cup. Bolton, Ont: Fenn Pub. pp. 12, 50. ISBN 978-1-55168-261-7.