- The Montreal Canadiens have won the most Stanley Cups with 24.
- Henri Richard has won 11 Stanley Cups, more than any other player to have played the game, all with the Montreal Canadiens.
- The Pittsburgh Penguins has the most recent dynasty with Sidney Crosby leading the charge.
What is a dynasty? Well to put it simply a dynasty is a team that dominates their sport for a lengthy period of time. The NHL has been around for over 100 years and in that time there have been many impressive Stanley Cup runs by various teams. This list will go through the most impressive dynasties of all time, of course, you'll find the Montreal Canadiens on this list (probably even more than once), a team that has won the most Stanley Cups (24).
10. The Montreal Canadiens: 1964-69
From the years 1964 to 1969 the Montreal Canadiens went on a very impressive win streak. They won four Stanley Cups in six years. This is only one of two dynasty eras from the Montreal Canadiens in the 60s, you'll see the other one later on in the list. The Montreal Canadiens in the 60s were a force to be reckoned with, in the three of four cup wins, the team also finished first during the season. Leading the pack was Jean Beliveau, arguably the best Montreal Canadien to ever play the game.
9. Toronto Maple Leafs: 1944-1951
From 1944 to 1951 the Toronto Maple Leafs won a total of five Stanley Cups. Some would say that Ted Kennedy or "Teeder" as some would call him was a great help towards leading the Toronto Maple Leafs to go on the fantastic run that they did. It's important to note, that in these 5 Stanley Cup wins, the Leafs finished first in only one of those seasons, making them a true underdog team. Unfortunately for the current Toronto Maple Leafs fans, this was the most successful the Leafs had ever been to date.
8. Chicago Blackhawks: 2009-2015
The Chicago Blackhawks are one of this list's more modern Dynasty. Between 2009 and 2015 they won a total of three Stanley Cups. While that wouldn't seem that impressive to some, in the modern day NHL, winning the Stanley Cup is quite difficult, and winning multiple within a few years, well that's downright impressive. This Chicago Blackhawks dynasty was lead by Jonathan Toews, Duncan Keith, and Patrick Kane.
7. Edmonton Oilers: 1983-90
The Edmonton Oilers were unstoppable in the 80s. And we have two words for you that will explain why: Wayne Gretzky. Wayne Gretzky is the best hockey player of all time, no wonder people call him "The Great One". The 80s were Gretzky's prime years of playing and he leads the Edmonton Oilers to four of the five Stanley Cups. The last Stanley Cup in 1990 was won without Gretzky as he was traded away to the Los Angeles Kings by that time. The team however did have the likes of Mark Messier, Paul Coffey, and Kevin Lowe to get them their 5th cup in 7 years.
6. New York Islanders: 1980-84
The New York Islanders were the true face of resilience at the time. Prior to the 1980 season, the Islanders hadn't even gotten past the semi-finals of the Stanley Cup playoffs since 1972. But once the floodgates were open the team dominated and won 4 Stanley Cups in a row. This is the last team to have ever won four Stanley Cups in a row, the only team to have come close was the Washington Capitals who won two championships in a row in recent years. The New York Islanders set an all-time record of 19 consecutive playoff series wins.
5. Montreal Canadiens: 1952-60
Remember how we mentioned above that the Montreal Canadiens had two dynasties featured in the 60s? Well, this is the second one. And spoiler alert, the Montreal Canadiens are not finished being featured on this list. Between 1952 and 1960 the Montreal Canadiens won 6 total Stanley Cups. This was a great time to be a Habs fan, you got to see Maurice Richard and Jean Beliveau light up the ice.
4. Detroit Red Wings: 1996-2002
This is our second "modern-day era" hockey dynasty featured on this list. While it seems like a lengthy period of time, '96 to 2002, this dynasty shouldn't go unnoticed. The Detroit Red Wings won a total of three Stanley Cups in this time, but it's more than just the cups. This team was a force to be reckoned with throughout those 8 years.
The team also achieved grabbing four conference titles, six of eight of their seasons finished with a points percentage of over .600 and on top of all that, they finished in first place five times. Yeah, we'd call that a successful dynasty.
3. Detroit Red Wings: 1947-1956
Nope, you didn't misread, the Wings make the list again. from 1947 to 1956 the Detroit Red Wings won four Stanley Cups in 9 years. This 9-year dynasty gave us the amazing, Mr. Hockey Gordie Howe. In 1952 the Red Wings went on to dominate in literally every category, from most goals, fewest goals against and they never lost a single game in the playoffs. We couldn't do a list of NHL dynasties and not include Gordie Howe's Detroit Red Wings.
2. Pittsburgh Penguins: 2009- Present
The Pittsburgh Penguins have the longest dynasty on this list well because...it's still going on. Since 2009, they have won three Stanley Cups, and the new "greatest of all time" Sidney Crosby has been leading the charge. The third modern-era dynasty has also appeared in the post-season a whopping 12 times as well. Sidney Crosby is only 32 years old and has a lot of hockey left, who knows how many more Stanley Cups he will hoist above his head again.
1. Montreal Canadiens: 1970-79
Coming in at number one on our list is the team that literally dominated a century. The Montreal Canadiens won six Stanley Cups in 9 seasons, as well as winning four of those cups in a row between 1976 and 1979. In this time they also had seven first-place finishes and their last Stanley Cup team featured 10 Hall Of Fame players, the most of any winning team.
The Montreal Canadiens last Stanley Cup win was over 27 years ago, so we can't know for sure if they have a future dynasty in-store any time soon.