The last team to win four Stanley Cups in five years is the Edmonton Oilers. The last team to win five Cups in a seven-season span is also the Oilers. Few teams have even had an outside chance at matching those feats since. Even the current-day Florida Panthers face a tall task in trying to match that success.
As far as dynasties go, the 1984-1990 Oilers are the most recent “true” dynasty, if we’re to include certain benchmarks. But a question arises: where do those Oilers rank among all the dynasties in NHL history? Which legacy-laden repeat champs even merit consideration for that label?
This observer is putting all fan bias aside, and taking this task head-on. Time to cover a lot of ground- and a lot of greatness- in this one story.
Honourable mention: 1990s to 2000s Detroit Red Wings
Post-1990, there has not really been a whole lot in the way of dynasty teams. In the 17 seasons following this era of ‘Wings hockey, only two teams have won more than two Cups. Those were the Pittsburgh Penguins, who won in 2009 and then had to wait seven more seasons to go back-to-back with Cup wins, and the 2010 to 2015 Chicago Blackhawks, who were likely denied dynasty status by the 2014 Los Angeles Kings winning in Overtime of Game 7 of the Western Conference Final.
Since 1992, following the other Penguins repeat, only one team boasts more than three Cups. That would be these Yzerman/Lidstrom-era Red Wings, overseen by current Kings and former Oilers General Manager Ken Holland. Like the Blackhawks, a WCF loss in 1996 is probably what holds the Yzerman portion of this era back from dynasty status.
However, this is undeniably the greatest “era” for any NHL team since the early-90’s expansion boom. Four Cups in 11 years, making it back to the top in 2008, post-lockout. Doing so even without Yzerman, or Scotty Bowman as Head Coach. The 2002 Red Wings alone had 10 future Hall of Fame players, a HoF Head Coach, and HoF GM. These ‘Wings have yet to be matched by any other team since.
8. 1940’s Toronto Maple Leafs
This is probably the obvious choice to be docked a bit, though you can’t fault them for having two of their Cups in that decade (1942 and 1945) be impacted by an entire World War. Even still, until 2024, 1945 was the last time a 3-0 Stanley Cup Final ended up going the full seven games. Dynasties don’t typically let opponents, in this case the Red Wings, back into series to that extent.
Due to World War II, a lot of usual NHL players were absent from the league, as the 1945 squad in particular didn’t have too much beyond Ted Kennedy in the way of star power. Things picked up by the time of their 1947-1949 three-peat, however. Goaltender Turk Broda, captain Syl Apps, and other big names such as Kennedy, and Bill Barilko joined. So while the three-year was impressive, calling this a “dynasty” is a bit of a stretch. Technically, it is. But that first of four Cups in five years is quite iffy.
7. 1950’s Detroit Red Wings
Don’t get this observer wrong; these Wings had immense talent. Anytime you have a storied nickname for an entire line, you have achieved greatness. And indeed, the trio of Gordie Howe, Sid Abel, and Ted Lindsay formed the “Production Line” that flourished like Detroit’s auto industry of the time. Add on having Terry Sawchuk as your goalie, and you have a recipe for success.
Reigning as champs, however, proved difficult for this group. They won the first of their four Cups in 1950, immediately as the previous Leafs dynasty ended. They would have to wait a year before winning again in 1952, then repeat that process. 1954 and 1955 were the only time the Wings went back-to-back during the Gordie Howe era.
Four Cups in six years is still pretty darn impressive no matter how you slice it. However, only managing a single repeat of a championship dampens its standing among other dynasties. At the very least, they prevented an upcoming dynasty on this list from being even longer and more storied.
6. 1960’s Toronto Maple Leafs
The Oil Rig will respectfully refrain from any “1967” jokes, or lamenting about how both Leafs dynasties happened in what was only a six-team NHL. 6ix On Ice, our sister site, would not take kindly to it. But even beyond those, this dynasty can’t possibly be ranked higher than sixth.
Like with their 1940s brethren, the 1960’s Leafs had a three-peat from 1962 to 1964, and then returned to the top with the noted last triumph. Unlike those Leafs, there were no vanquished three games to none leads. Only one time (1963) did they need seven games to clinch the Cup.
Frank Mahovlich, Tim Horton, Red Kelly, Dave Keon, George Armstrong, Johnny Bower. There were so many star players on those Leafs teams, and star personalities, too. One of them even had his own donut shop up and running by the time the Leafs got Cup number 4.
Alas, a donut is all they have following Canada’s Centennial year. In all seriousness, if there was ever a year for them to make it back to the Final, this would be a good one. Do it for Joe Bowen.
5. 1965-1971 Montreal Canadiens
Like the Oilers of twenty years later, these Habs won five Cups in seven years. They even did it with the same pattern of repeat, one-year break, repeat, one-year break, fifth Cup. So how was this tie broken?
If you choose to lump 1973 into this process, that makes six Cups in nine seasons for les Canadièns. However, this ranking determined it this way: The first of the two Cup repeats happened when there were still six NHL teams, and the second of the two Cup repeats happened against an expansion St. Louis Blues squad not yet ready for the intensity of the Stanley Cup Final. By level of difficulty, this five-in-seven stretch was easier to achieve.
The talent was still incredible. Jean Beliveau, Yvan Cournoyer, Serge Savard, and the “Pocket Rocket” Henri Richard. Gump Worsley in net, although 1971 would bring along a new face who will be mentioned later on. This team was built to win Cups, no doubt. But they had it easier than the next entry.
4. 1984-1990 Edmonton Oilers
The ’80s Oilers are unquestionably a top-five dynasty of all time. Heck, the 1984-85 squad alone was voted as the greatest NHL team ever. All the names this Lookbacks series has covered, their record-setting ascent to the summit of Lord Stanley. All of that proves that this core was truly as great as is boasted.
The one thing holding this dynasty back is that it could not three-peat a single time. Five Cups in seven years is a fantastic run, no doubt, especially in a 21-team league. But the top three all have runs of at least four Cups in a row.
1986 will likely be the greatest “what-if” ever. If a fluky own goal wasn’t scored versus Calgary, if the Oilers drive for five like their city’s football team had just done not long beforehand. Does this team rise to the top of the list?
Hard to say. But for now, fourth place still puts them in the upper half of all NHL dynasties. As is deserved.
3. 1976-1979 Montreal Canadiens
Our condolences go out to the Montreal Canadiens and the family of Ken Dryden, who sadly passed away last week. Dryden was a major piece of this dynasty; after helping the Habs to 1971 and 1973 triumphs, he stuck around and backstopped a four-peat before retiring in his prime to go contribute to society in a myriad of other ways. Dryden was one of the greatest at “doing it all,” in this observer’s eyes.
Beyond Dryden, Cournoyer and Savard were still around to lead the team’s charge. Stars like Guy Lafleur and Pete Mahovlich also boosted this team to dynasty status. Others, such as Doug Jarvis and Larry Robinson, also proved to be pretty helpful.
Like the next entry on the list, their dynasty was a four-peat. The tiebreaker, once again, was in difficulty. The tiebreak winner would have to contend with a 21-team league, including two separate challenges from a young, hungry Oilers squad before succumbing to a third. The Habs had it slightly better off in the 1970s, so third place it is.
2. 1980-1983 New York Islanders
It was documented in earlier Lookbacks why this bunch was such a storied dynasty in its own right. That still remains as truth, and holds greater weight here. Keeping in mind, the Oilers gave them as much as they could handle in 1981, right after knocking out the still-mighty Habs whose dynasty had just concluded.
After a six-game triumph in 1980, the Islanders would only lose one more Cup Final game over the next three years, en route to their own four-peat. They were largely as automatic of Champions as you could get. And when you look at their own core, you see why right away.
Mike Bossy, Bryan Trottier, Clark Gillies, Butch Goring, and goaltender “Battlin’ Billy” Smith, along with John Tonelli and 1980 Cup Final hero Bob Nystrom, gave this lineup supreme power. They used it to lord over the NHL for the first four years of the 1980’s. They are still the most recent four-peat champs in NHL history, and it may stay that way forever.
1. 1950’s Montreal Canadiens
Yes, this happened during the Original Six era, and that means they had “easier” paths to Cups, so to speak. However, this is undeniably the greatest dynasty in NHL history, for many reasons. Some are plain facts, the others more underlying.
No other team in NHL history has won five Cups in a row, for starters. The Islanders nearly did, but even they fell short. Tack on a 1953 Stanley Cup, and the Habs won six Cups in eight years with essentially the same core.
Here’s what makes its case even stronger, though. The Canadiens went to nine Stanley Cup Finals in a row, a record that will surely never be broken given the degree of difficulty in today’s NHL. If not for the Howe-era Red Wings, this well could have been eight Cups in a row.
Of course, when you have talents like Beliveau, Maurice Richard and his brother Henri, Bernie Geoffrion, and a stud goalie in Jacques Plante, you’re bound to win a title or three. Or five, in the Habs case. This is an insane run of glory that may never be equalled in the rest of NHL history. As such, these Habs will forever be at the top of the all-time dynasties list.
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