Regardless of if your team boasts the Art Ross Trophy winner or even makes it back to the playoffs for the first time in years, in the end, all that really matters in the NHL is winning the Stanley Cup.

Last season, the Vegas Golden Knights won their first Stanley Cup, getting the better of the Cup-less Florida Panthers in five games.

In the league’s storied history, Canadian teams have dominated, but in some measures of NHL success, teams not nicknamed “the Habs” can also lay claim to being the most successful NHL team. 

Which Team has the Most Stanley Cup Wins?

The Montréal Canadiens have the most Stanley Cup wins by a considerable margin. From their first in 1916 to their most recent triumph in 1993, the Habs have won the Stanley Cup 24 times. 

In 1956, the Canadiens got running on an imperious streak of Stanley Cup wins, going on to claim the 1957, 1958, 1959, and 1960 titles. From 1965 to 1971, the Habs made it to the Finals six times to hoist the massive trophy five more times.

Next in line to the Habs are the Toronto Maple Leafs. Way back with only 13 Stanley Cup wins, the Buds were dominant in the 40s and went head-to-head with Montréal in the 60s, marking the team’s last Finals victory in 1967. 

This season, fans and oddsmakers are backing the Buds to close the gap on the wins leaders. In the NHL betting, the Toronto Maple Leafs lead the way as the Stanley Cup favourites with odds of +800.

Which Team has Gone to the Most Stanley Cup Finals?

As you would have guessed, the Montréal Canadiens have been to the most Stanley Cup Finals, getting to the decisive series 35 times, winning the Cup on 24 of those occasions.

Montreal Canadiens have reached more Stanley Cup finals than any other team

The Habs were also the last Canadian club to make it to the Finals, going on a remarkable run against the odds in 2021 only to fall to the Tampa Bay Lightning in five games.

After the Habs, it’s the Detroit Red Wings with 24 showings at the Stanley Cup Finals, and then the Maple Leafs with 21 shots at the crown. 

Next in line is the Boston Bruins with 20. Given the records that they smashed during the 2022/23 regular season, there would have been a large cohort of hockey fans backing the Bs to at least climb to 21 Finals. 

Which NHL Team has Made it to the Playoffs the Most?

Boasting 85 trips to the playoffs in their 114-year history, the Montréal Canadiens also claim this title of NHL success. 

Not so far behind the Habs, however, are the Bruins with 76 playoff seasons, but that’s not an overly favourable count when you see that the Bruins have only converted six of those into Stanley Cup wins.

Which US Team has Won the Most Stanley Cups?

Canadian teams dominate the NHL history books, but the Detroit Red Wings have certainly enjoyed a few prolonged spells of NHL success and boast 13 Stanley Cup wins to lead all US-based teams.

Their first came in 1936, which was followed by their second in the very next season. The Red Wings would make it to several Finals after this, won it again in 1943, but the team’s first extended run of success came in the 50s.

With wins in 1950, 1952, 1954, and 1955, Detroit brought the Stanley Cup tally up to seven. Back-to-back triumphs in 1997 and 1998 put distance between them and the Bruins in the wins chart, and then two more came their way in 2002 and 2008.

Red Wings Successful US Team NHL

However, the Red Wings have been in a kind of limbo for several years now. After a headline-grabbing trade for Alex DeBrincat, general manager Steve Yzerman is clearly trying to get playoff hockey back to Detroit. 

How well the sniper gels with his new team is yet to be seen, but there’s a decent roster being pulled together in Detroit now. If they get off to a hot start, it’d be worth keeping tabs on them in the live betting online

Which NHL Team has the Highest Stanley Cup Finals Win Percentage?

The Colorado Avalanche have the highest Stanley Cup Finals win percentage at 100%. In each of the three seasons that the Avs have made it to the Finals, the team once known as the Québec Nordiques have taken home the Cup.

In a cruel twist of fate for the hockey faithful in Québec, the Avs won their first Stanley Cup in the same season that the club left Canada for Denver. 

In 2001, Colorado made it to the Finals again to claim the crown. This season, they’re returning as one of the Western Conference heavyweights after a strong offseason, looking to capitalise on the momentum of winning the Cup in 2022. 

Which Non-Original Six Team Has the Most Stanley Cup Wins?

Outside of the Original Six, which was established between 1917 and 1926, the Pittsburgh Penguins (founded 1967) and Edmonton Oilers (founded 1972) boast the most Stanley Cup wins at five apiece.

Depending on how you look at it, you could say that the Oilers are more successful than the Penguins as they’ve made it to seven Finals to Pittsburgh’s six. On the other hand, the Pens have a higher win percentage in the Finals.

Of the two, the Oilers are clearly favoured to add to their tally and break this tie for the crown of the most successful NHL team that’s not a part of the Original Six. 

Overall, the Montréal Canadiens are the most successful team in NHL history, and in most regards, it’s not even a close race.


*Credit for all images in this article belongs to AP Photo*

Ben is very much a sports nerd, being obsessed with statistical deep dives and the numbers behind the results and performances.

Top of the agenda are hockey, soccer, and boxing, but there's always time for the NFL, cricket, Formula One, and a bit of mixed martial arts.