Which Team Has Won the Most Stanley Cups in a Row?

The days when a team could win four or five straight Stanley Cups are long gone. 

It hasn’t happened in over 40 years, and thanks to the salary cap, an abundance of teams, and NHL Commissioner Gary Bettman’s continual obsession with maintaining parity, the chances of it occurring again are slim. 

Most Consecutive Stanley Cup Wins

The Montreal Canadiens won five Stanley Cups in a row from 1956 to 1960, the most of any franchise since 1927, when the WHL folded, making the NHL the only remaining league. 

However, there should probably be a Zdeno Chara-size asterisk beside that five-year winning run, as the Canadiens were one of just six NHL teams. 

Starting each season with a 17% chance of winning the Stanley Cup sounds like a fantasy for current NHL franchises, who have 1-in-32 odds of winning it all (3%). Of course, Stanley Cup odds differ as they consider many factors, including each team’s overall ranking and talent.

The record stands, whether you accept the Canadiens’ five Stanley Cups in a row or not. You probably won’t be surprised to learn that the Montreal Canadiens are also the NHL’s most successful team. 

Franchises That Won Four Stanley Cups in a Row

The Canadiens and New York Islanders are the only two NHL franchises that have won four Stanley Cups in a row. 

The Canadiens reeled off four Stanley Cups in a row from 1976 to 1979. The first of their four Cup triumphs occurred just two years after the NHL expanded from 12 to 18 teams. So the Chara-size asterisk from their five straight Cups doesn’t apply to the four-Cup run. 

The New York Islanders’ four successive Stanley Cups are arguably more impressive. They achieved the improbable feat after the NHL expanded to 22 teams in 1979. It was the last time a franchise put together a consecutive run of more than two Stanley Cups. 

Franchises That Won Three Stanley Cups in a Row

Excluding the aforementioned four and five-year runs, the Toronto Maple Leafs are the only franchise that has won three in a row. Their two three-peats came 13 years apart. The first occurred from 1947 to 1949, and the second from 1962 to 1964. 

However, like the Canadiens’ five-peat, Toronto’s three-peats came when just six teams competed. 

Which Franchises Have Won Back-To-Back Stanley Cups Since 1983?

The Islanders’ four consecutive Stanley Cups in the early 1980s marked the end of an era. There have been only six back-to-back Stanley Cup winners since that remarkable Islanders’ dynastic run over 40 years ago. 

Of the six back-to-back winners, the Pittsburgh Penguins and Edmonton Oilers have four. The Oilers’ first back-to-back run came after the Islanders’ four-peat. In 1983-84, the Oilers defeated the Islanders in the Stanley Cup Final, preventing New York from winning its fifth straight. 

The following season, in 1984-85, saw the Oilers defeat the Philadelphia Flyers in five games to win their second straight Stanley Cup.

The Oilers failed to make it three in a row in 1985-86, with the Canadiens prevailing over the Calgary Flames in the final. The Oilers rebounded the following season and won two successive Stanley Cups, making it two repeats and four Stanley Cups in five years. 

The Penguins secured their two back-to-back successes 25 years apart, each led by a generational talent. Mario Lemieux was the driving force behind the Pens’ 1991 and 1992 Cup victories, while Sidney Crosby was at the helm in 2016 and 2017.

The Detroit Red Wings won consecutive Stanley Cups in 1997 and 1998, while the Tampa Bay Lightning were the most recent franchise to accomplish the rare feat, winning in 2020 and 2021. They came within a whisker of winning three straight but lost in the 2022 Stanley Cup Final to the Colorado Avalanche in six games.