5. Detroit Red Wings
> Consecutive winning seasons: 24 seasons
> Seasons: 1991-1992 to 2015-2016
> Championships: 4 Stanley Cups
> Notable players: Steve Yzerman, Nicklas Lidstrom
In the 1990s, the Detroit Red Wings were mired in a Stanley Cup drought that stretched all the way back to 1955. Coach Bryan Murray got the franchise turned around, taking the Red Wings back to the playoffs in 1991 and back to a winning record for the 1991-1992 season. He was replaced by Scotty Bowman in 1993, who led the Wings to three Stanley Cups in the next decade. Even after Bowman retired, Detroit kept winning, bolstered by the skills and leadership of Nicklas Lidstrom and Steve Yzerman — both of whom played for Detroit for at least 20 seasons. The Red Wings won the Cup in 2008 and made the playoffs every year until 2016-2017.
4. New York Yankees
> Consecutive winning seasons: 27 seasons
> Seasons: 1993 to present
> Championships: 5 World Series
> Notable players: Derek Jeter, Aaron Judge
The model of class and consistency, the New York Yankees are adding onto their lengthy streak of winning seasons. New York hasn’t had a losing season since 1992, bolstered by legends like Mariano Rivera, Derek Jeter, and numerous others. The Bronx Bombers have won five titles during this stretch, the most recent in 2009. The Yankees now have a young core of stars like Aaron Judge, and they show no signs of putting up a below .500 season any time soon.
3. Boston Bruins
> Consecutive winning seasons: 29 seasons
> Seasons: 1967-1968 to 1995-1996
> Championships: 2 Stanley Cups
> Notable players: Bobby Orr, Ray Bourque
From the late 1960s to the mid 1990s, the Boston Bruins never missed the playoffs. After an eight-season playoff drought beginning in 1960, coach Harry Sinden righted the ship, steadily improving the Bruins until they won the 1970 Stanley Cup. The Bruins won it again in 1972, led by superstar defenseman Bobby Orr. Despite shuffling through a dozen different coaches from 1967 to 1996, the Bruins made the playoffs during each of those seasons. Yet, for the duration of that streak, the Bruins could only win the two Stanley Cups in 1970 and 1972. The team made five Finals appearances after that but could never bring home the Cup.
2. Montreal Canadiens
> Consecutive winning seasons: 32 seasons
> Seasons: 1951-1952 to 1982-1983
> Championships: 16 Stanley Cups
> Notable players: Maurice Richard, Jean Beliveau
The Montreal Canadiens saw unprecedented success in the NHL for almost the entire 20th century. The team, founded in 1917, won at least one championship in every decade it existed until the 2000s. The most successful period came from 1951 to 1983 — a 32 season stretch in which the Habs posted 21 straight winning seasons, missed the playoffs just once, and won 16 Cups. Stars like Maurice Richard, Guy LaFleur, and Jean Beliveau came and went, but the outcomes stayed the same as the Canadiens racked up Cups in bunches. Yet Montreal is now mired in its longest Cup drought in history, its last title coming in 1993.
1. New York Yankees
> Consecutive winning seasons: 39 seasons
> Seasons: 1926 to 1964
> Championships: 19 World Series
> Notable players: Babe Ruth, Joe DiMaggio
No team has ever come close to the greatness achieved by the 20th century New York Yankees. From 1926 to 1964, the Yanks never had a losing season — 39 years. In 19 of those 39 seasons, the Bronx Bombers also won the World Series. For context, no other MLB franchise has more than 11 championships total. The Yankees’ stars of that era are still among the greatest to ever play ball — stars like Babe Ruth, Joe DiMaggio, Lou Gehrig, Yogi Berra, and Mickey Mantle to name a few.