The “most winningest” team in hockey

Rob Boudreau
July 23, 2009

Last April, I wrote about the “most winningest” team in sports, and based on the success of the story, have decided to take a deeper look into the numbers behind the experiment. For the next four weeks, I’ll be dissecting the four major sports and the teams that have won the respective coveted prizes in each. This week: hockey.

First, let’s clear things up before they get confusing. What you probably know is that the National Hockey League’s coveted prize is the Stanley Cup, and it has been sought after and won since 1915. What you probably don’t know is that only a total of 84 NHL teams are recognized as having won the championship. Based on the rules of the aforementioned article, our study will focus on those 84 champions, regardless of how long they’ve existed, even if they came before the NHL we have today.

The Montreal Canadiens have won the most Stanley Cups in the NHL, with 24 titles dating all the way back to 1916 when the league was still known as the National Hockey Association. With these 24 wins in 100 years of existence, their championship winning percentage (CWP) is a solid 24 per cent. But, thanks to the previous story, we already knew that.

The next closest in the list are the rival Toronto Maple Leafs with 13 titles in 92 years (14.13 CWP). What makes them interesting is the fact that, although they are second on the list, the last time they won was 1967, a fact too-well known to fans of the Blue and White. The sad part about the Leafs’ victories is that 1967 was the last year that the NHL existed as a divisionless, six-franchise league (giving each team great odds to win compared to teams playing today).

However, there is a team that appears to be even more useless than the Leafs – the Chicago Blackhawks. Another Original Six era team, the Blackhawks have just three Cups in 83 years (3.61 CWP), the last coming in 1961. It seems unbelievable, considering the team of the early ’90s with players like Jeremy Roenick, Chris Chelios, and Ed Belfour, yet not even they could snap what is now the NHL’s longest drought among teams who have at one point tasted the Cup.

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The New York Rangers take the title of “fastest winningest.” In only their second year of existence, 1928, the Rangers won the Cup. Outstandingly, over the next eight seasons, each of the Original Six teams won the Cup at least once.

The Philadelphia Flyers look to be suffering a similar fate. At one point they appeared as if they were going to be a powerhouse franchise in the NHL. The Broad Street Bullies won the Stanley Cup in 1974, in just their seventh year in the league, and actually repeated in ’75. Unfortunately they haven’t won since, despite having taken their division a total of 15 times.

Back in the early ’30s, nearly two decades after it was first awarded, the Cup saw its first repeat champion. In 1930 and 1931, the Canadiens won their third and fourth titles. The Maple Leafs three-peated from ’47-’49, but the Canadiens dominated hockey in the following decade, winning six Cups, including five in a row, from ’56-’60.

With the coming of the NHL expansion era in 1967, the league created divisions. Since then, a team that has won its division has also won the cup 28 out of 41 times (68%). Last month, the Pittsburgh Penguins became the first team since 2000 to win after having lost their division. Of the teams who have won the Stanley Cup only once – the Ducks, Flames, Lightning, Hurricanes and Stars – all five won their divisions as well.

Going back to 2000, the Martin Broduer-led New Jersey Devils won their second Cup after losing their division. Although, finishing with 103 points in the regular season, they were just two behind the first-place Flyers. In ’99 and ’01, the Devils won the Atlantic Division, yet lost in the first round and finals, respectively.

Any team can win the Cup once. It takes a great team to repeat. This has happened 24 times. Although some would argue that the Canadiens’ victories in the late ’50s were a great run of repeats, nothing stands out more than the period between 1976 to 1988 when just three teams split 13 Stanley Cups. If you consider the modern day Penguins or Red Wings to be dynasties, then these teams were empires.

It went like this: Montreal Canadiens from ’76-’79, New York Islanders from ’80-’83, Edmonton Oilers from ’84-’85, Canadiens again in ’86 and then Oilers twice more in ’87 and ’88. If it weren’t for the Calgary Flames squeaking out a seven-game series win over the Oilers in ’89, in which they may have had their greatest team and greatest player, Wayne Gretzky, the Oilers could easily have had a string of five in a row themselves.

The Islanders won those four in a row with the first coming in just their eighth year of existence. The last of their streak, in 1983, is their most recent triumph. With players like Mike Bossy and Bryan Trottier, was this team a dynasty? Perhaps. Although they never finished the season with more than 50 wins, they managed to go 60-18 during their four years of playoff success.

Since then, few teams have remained in the conversation with Stanley Cup potential for an extensive amount of time, the one obvious exception being the Detroit Red Wings.

The Wings are arguably one of the greatest teams in history, having made the playoffs in all of the last 18 seasons and 23 out of 25, which is the longest streak in professional sports. In the last 15 years, the Red Wings have won four Stanley Cups. Two of those four came when they had lost their division (’97 and ’98), which they only did three times in that span. The ’97 and ’98 titles are also the last time a team has repeated as NHL champion.

Although it is easy to call the Canadiens the “most winningest” team in the NHL thanks to their 24 Stanley Cups, it becomes a much different story when you consider the level of competition. Five opponents differs greatly from the 29 opponents teams face today, but 24 Cups is still almost double that of the next closest.

Next week, come back and see how the Green Bay Packers’ 12 league championships holds up against the rest of the NFL.

The table below is accurate as of June 15, 2011. The article itself is only accurate of its publication date. -TheGP

Team EST. Years Wins CWP
Montreal Canadiens 1909 102 24 23.53
Toronto Maple Leafs 1917 94 13 13.83
Edmonton Oilers 1972 39 5 12.82
Detroit Red Wings 1926 85 11 12.94
New York Islanders 1972 39 4 10.26
New Jersey Devils 1974 37 3 8.11
Boston Bruins 1924 87 6 6.90
Pittsburgh Penguins 1967 44 3 6.82
Anaheim Ducks 1993 18 1 5.56
Tampa Bay Lightning 1992 19 1 5.26
Colorado Avalanche 1972 39 2 5.13
Chicago Blackhawks 1926 85 4 4.71
New York Rangers 1926 85 4 4.71
Philadelphia Flyers 1967 44 2 4.55
Calgary Flames 1972 39 1 2.56
Carolina Hurricanes 1972 39 1 2.56
Dallas Stars 1967 44 1 2.27
Buffalo Sabres 1970 41 0 0.00
Columbus Blue Jackets 2000 11 0 0.00
Florida Panthers 1993 18 0 0.00
Los Angeles Kings 1967 44 0 0.00
Minnesota Wild 2000 11 0 0.00
Nashville Predators 1998 13 0 0.00
Ottawa Senators 1992 19 0 0.00
Phoenix Coyotes 1972 39 0 0.00
San Jose Sharks 1991 20 0 0.00
St. Louis Blues 1967 44 0 0.00
Vancouver Canucks 1970 41 0 0.00
Washington Capitals 1974 37 0 0.00
Winnepeg Jets 1999 12 0 0.00


(July 30) – The “most winningest” team in football

(August 6) – The “most winningest” team in basketball

(August 13) – The “most winningest” team in baseball

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The Author:

Rob Boudreau