Since the Stanley Cup was dedicated to NHL's top team in 1926, only five franchises (Toronto Maple Leafs, Detroit Red Wings, Montreal Canadiens, Boston Bruins, St. Louis Blues) have qualified for consecutive Cup Finals and lost each time. Nine times the losing streak was limited to two years though twice a three year streak struck (Toronto 1938-1940, St. Louis 1968-1970). The charts below describe these streaks by team and years, and vice versa.
The record for consecutive Stanley Cup wins by the same club is five (Montreal 1956-1957-1958-1969-1960) with two teams managing four straight wins (Montreal 1976-1977-1978-1979, New York Islanders 1980-1981-1982-1983), one team duplicating three year streaks (Toronto 1947-1948-1949 & 1962-1963-1964), and four squads posting one or more pairs (Detroit 1936-1937 & 1954-1955 & 1997-1998, Philadelphia 1974-1975, Edmonton 1984-1985 & 1987-1988, Pittsburgh 1991-1992 & 2016-2017, Tampa Bay 2020-2021).
The charts below describe these streaks by team, years, and vice versa.
Prior to Tampa Bay turning the trick in 2021, Pittsburgh was the last team to appear in consecutive Stanley Cup Finals (2016, 2017) when they beat San Jose and Nashville, respectively..
The last team to win the Stanley Cup three times in a row was the New York Islanders (180, 1981, 1982, 1983), though Tampa Bay came within two games of a three-peat before losing to the Colorado Avalanche in game 6 of Stanley Cup final.
On June 13th of 2023, Jonathan Marchessault became the 48th Canadian, 4th left winger, 2nd undrafted player, and 1st Vegas Golden Knight to earn the honor. Tim Thomas is the eldest recipient of the award at age 37 (2011), while Patrick Roy remains the youngest at age 20 (1986).
The chart below describes, in descending order, the number of seasons each of these 24 teams has gone without winning a series in the Stanley Cup playoffs, showing the last year they actually won a postseason series.
In 2023, the Toronto Maple Leafs ended a 17 season winless streak where they qualified for the playoffs 7 times and fell to their first round opponent every time (Boston 2013, Washington 2017, Boston 2018, Boston 2019, Columbus 2020, Montreal 2021, Tampa Bay 2022). 5 of the 7 series saw the Maples Leafs lose in a deciding game 7, including all 3 series against Boston ... one of which they held a 4-1 third period lead (2013) only to collapse in spectacular fashion before the final buzzer.
This year it was Boston's turn to implode as the President's Trophy winning squad squandered a 3-1 series lead and a 3-2 lead in the final minute of Game 7 to fall to Florida in overtime and extend their drought.Playoff berths are harder to come by every year. Make the most of each opportunity as parity promises your window will likely quickly close.
