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Teams With the Most Stanley Cups (Ranked)

The Stanley Cup is the oldest and most prestigious trophy in North American professional sports, awarded annually to the NHL's championship team since 1893 (and exclusively to NHL champions since 1927). Over 109 championships, 20 franchises have hoisted the Cup, but only a handful have built true dynasties. Here's the definitive ranking of teams by total Stanley Cup victories.

January 25, 2026

Tier 1: The Dynasty Elite

The franchises that defined championship hockey:

1. Montreal Canadiens (24 Stanley Cups)

The most successful franchise in NHL history.

34 Finals appearances, .706 win percentage
Last Cup: 1993
Longest streak: 5 straight (1956-60)
Four straight Cups (1976-79)

Montreal's 24 championships are 10 more than any other team. Their dominance spans multiple eras with dynasties built on Maurice Richard, Jean Béliveau, Doug Harvey in the 1950s, then Guy Lafleur, Larry Robinson, Ken Dryden in the 1970s. However, the Habs are currently in a 32-year Cup drought, longest among Original Six teams.

2. Toronto Maple Leafs (13 Stanley Cups)

Second most Cups but longest active drought.

21 Finals appearances, .619 win percentage
Last Cup: 1967
Won three straight twice (1947-49, 1962-64)
58-year championship drought (longest in NHL)

Toronto's 13 Cups rank second, but their 58-year drought is cultural touchstone for hockey's most valuable franchise ($2.8B). The 1940s dynasty featured Ted Kennedy and Turk Broda. The 1960s run showcased Frank Mahovlich and Dave Keon. Despite star-laden roster (Matthews, Marner, Tavares), playoff struggles continue.

3. Detroit Red Wings (11 Stanley Cups)

Only U.S.-based team with double-digit Cups.

24 Finals appearances, .458 win percentage
Last Cup: 2008
Three distinct eras: 1930s, 1950s, 1990s-2000s
"Hockeytown" nickname

Detroit's 11 championships came in waves. The 1950s featured Gordie Howe, Ted Lindsay, Terry Sawchuk. The modern dynasty (1997-2002) showcased Steve Yzerman, Nicklas Lidström, Sergei Fedorov. Since 2008, Detroit has missed playoffs six straight seasons, rebuilding through draft (Moritz Seider, Lucas Raymond).

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4. Boston Bruins (6 Stanley Cups)

Six Cups but most Finals losses (14).

20 Finals appearances, .300 win percentage
Last Cup: 2011
Notable droughts: 29 years (1941-70), 39 years (1972-2011)

The 1970 and 1972 Cups featured Bobby Orr, Phil Esposito, Johnny Bucyk. The 2011 championship, anchored by Tim Thomas's .940 playoff save percentage and Zdeno Chára's leadership, ended longest active drought at the time. Current core (Bergeron retired, Marchand, Pastrnak) remains competitive.

5. Chicago Blackhawks (6 Stanley Cups)

Two bursts of championship hockey.

13 Finals appearances, .462 win percentage
Last Cup: 2015
Three in Original Six era (1934, 1938, 1961)
Three in cap era (2010, 2013, 2015)

Chicago's 2010-15 run made them first cap-era dynasty, led by Jonathan Toews, Patrick Kane, Duncan Keith, Marian Hossa. Post-2015, full rebuild began with Connor Bedard (2023 first overall) as franchise cornerstone.

6. Edmonton Oilers (5 Stanley Cups)

Most dominant stretch of the 1980s.

7 Finals appearances, .714 win percentage (highest among teams with 3+ Cups)
Last Cup: 1990
Five Cups in seven years (1984-90)
Two straight (1984-85, 1987-88)

Wayne Gretzky, Mark Messier, Jari Kurri, Paul Coffey, Grant Fuhr created dynasty. Since 1990, Edmonton reached Final once (2006, lost to Carolina) and endured 16-year playoff drought (2007-22). Connor McDavid and Leon Draisaitl have restored contention.

7. Pittsburgh Penguins (5 Stanley Cups)

Best Finals win percentage among multi-Cup teams.

6 Finals appearances, .833 win percentage
Last Cup: 2017
Two straight (1991-92, 2016-17)
Only cap-era team to win consecutive Cups

Two dynasties defined Pittsburgh. Mario Lemieux/Jaromír Jágr won 1991-92. Sidney Crosby/Evgeni Malkin captured 2009, 2016-17. The .833 win percentage is elite (only lost 2008 Final to Detroit). Currently retooling with aging core.

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Tier 2: Strong But Not Dynastic

Successful franchises with multiple championships:

8. New York Islanders (4 Stanley Cups)

One of three teams to win four straight.

5 Finals appearances, .800 win percentage
Last Cup: 1983
Four straight (1980-83)

Bryan Trottier, Mike Bossy, Denis Potvin, Billy Smith dominated early 1980s. Only reached Final once since 1983 (2020, lost to Tampa). Remain playoff regular but haven't returned to Finals glory.

9. New York Rangers (4 Stanley Cups)

Four Cups across nine decades.

11 Finals appearances, .364 win percentage
Last Cup: 1994
Cups: 1928, 1933, 1940, 1994

The 1994 championship, led by Mark Messier, Brian Leetch, Mike Richter, ended 54-year drought. Currently contenders with Artemi Panarin and Igor Shesterkin.

10. New Jersey Devils (3 Stanley Cups)

Trap-era dominance.

5 Finals appearances, .600 win percentage
Cups: 1995, 2000, 2003
Built on neutral-zone trap and Martin Brodeur

Five Finals from 1995-2012 but lost in 2001 (to Colorado) and 2012 (to Los Angeles). Rebuilding around Jack Hughes and Nico Hischier.

11. Tampa Bay Lightning (3 Stanley Cups)

Most recent back-to-back champions.

5 Finals appearances, .600 win percentage
Last Cup: 2021
Two straight (2020-21)

Nikita Kucherov, Victor Hedman, Andrei Vasilevskiy led COVID-bubble championship and back-to-back. Nearly three-peated in 2022 but lost to Colorado. Remain Cup contenders.

12. Colorado Avalanche (3 Stanley Cups)

Elite win percentage.

4 Finals appearances, .750 win percentage
Cups: 1996, 2001, 2022
Second-best Finals win rate among 3+ Cup teams

The 2022 title, anchored by Cale Makar, Nathan MacKinnon, Mikko Rantanen, was first since relocating from Quebec. Perennial contenders in Western Conference.

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Tier 3: One or Two-Time Champions

Philadelphia Flyers (2 Cups: 1974, 1975)

"Broad Street Bullies" back-to-back champions. Bobby Clarke, Bernie Parent, Dave Schultz dominated mid-1970s. Reached six Finals since but lost each time, including 2010 to Chicago. .250 Finals win percentage among worst for multi-Cup teams.

Los Angeles Kings (2 Cups: 2012, 2014)

First 8th-seed to win Cup (2012). Jonathan Quick, Anze Kopitar, Jeff Carter led two championships in three years. Nearly three-peated but lost 2013 Conference Final to Chicago.

Single Cup Winners:

Calgary Flames (1989): Lanny McDonald, Joe Mullen, Mike Vernon. Lost Finals in 1986 (Montreal) and 2004 (Tampa).

Washington Capitals (2018): Alex Ovechkin's long-awaited championship. Evgeny Kuznetsov, Braden Holtby delivered clutch performances, ending 43-year drought.

St. Louis Blues (2019): Ultimate Cinderella story. Dead last in NHL on January 3, 2019, won first Cup behind Ryan O'Reilly and Jordan Binnington.

Anaheim Ducks (2007), Dallas Stars (1999), Carolina Hurricanes (2006): All won lone championship in 2000s.

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Teams That Haven't Won a Cup

Notable franchises still searching:

Buffalo Sabres: 55 seasons, two Finals losses (1975, 1999). Longest Cup drought among teams that reached Finals.
Vancouver Canucks: 55 seasons, three Finals losses (1982, 1994, 2011). Multiple heartbreaking Finals appearances.
San Jose Sharks: 34 seasons, one Final loss (2016). Competitive for two decades but never won.
Ottawa Senators (modern): 33 seasons, one Final loss (2007). Rebuilding after playoff runs in 2000s.
Arizona/Utah: 45 seasons, no Finals appearances. Recently relocated to Utah.
Winnipeg Jets: 45 seasons (counting Atlanta Thrashers years), no Finals appearances.

Historical Trends

Original Six Dominance

The Original Six (Montreal, Toronto, Detroit, Boston, Chicago, Rangers) own 43 of 65 Cups from 1942-1993 (66%). Pre-expansion monopoly and financial advantages created dynasties modern teams can't replicate.

Salary Cap Era Parity

Since 2005 salary cap, only Pittsburgh (2016-17) and Tampa Bay (2020-21) won consecutive Cups. Cap restrictions prevent sustained dynasties like Montreal's five straight or Islanders' four straight.

Win Efficiency Leaders

Pittsburgh (.833), Edmonton (.714), Islanders (.800) have best Finals win percentages among multi-Cup teams. Boston (.300) and Philadelphia (.250) have worst despite multiple championships.

The Verdict

Montreal's 24 Cups remain untouchable, 10 more than second-place Toronto. Detroit's 11 lead all U.S.-based teams. Pittsburgh (.833 Finals win rate) and Edmonton (.714) have most efficient championship records. Salary cap era has created parity, making back-to-back Cups rare and three-peats nearly impossible.

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