NHL Teams with the Most Stanley Cup Wins—Ever

Posted: November 9, 2015

Updated: October 6, 2017


• Montreal Canadiens are on top
• The Maple Leafs are due for a comeback
• The Bruins are back

Making predictions about who’ll be the next playoffs champion? Learn from history and take a look at the hockey teams with the most Stanley Cup wins since the NHL was founded in 1917.

Get NHL betting tips from times gone by at GamingZion in our spotlight article on NHL teams with the most Stanley Cup wins. While a couple of the teams’ positions have dropped in modern rankings and online sportsbooks in the US, there are still some that have stood the test of time and remain longstanding league all-stars.

#4: Boston Bruins

1929 Boston Bruins Staley Cup winners

The Bruins first won the Stanley Cup in 1929

Since the team’s beginnings in 1924, the Boston Bruins have snagged the Stanley Cup six times, having won in 1929, 1939, 1941, 1970, 1972, and 2011. The New England hockey team was founded in 1924 by grocery store financier Charles Francis Adam, who monumentally paid $15,000 to own and start up the first United States-based NHL team. Dozens of American hockey teams would go on to follow in their wake.

The Bruins have remained a solid team throughout history and continuously appear in US gambling news. They lacked Stanley Cup wins in the 1950s-1960s but were back in the playoffs and NHL hockey betting lines with a vengeance in the 1970s-1990s with legends like Bobby Orr, Terry O’Reilly, and Cam Neely. Things appeared a little shaky for the Bruins since the departures of these all-stars, but their 2011 Stanley Cup win—which ended a 39-year drought—marked a well-deserved comeback for the still-esteemed Bruins.

#3: Detroit Red Wings

1950 Detroit Red Wings Stanley Cup victory

Pete Babando held the cup for the Red Wings in 1950

The Detroit Red Wings were founded in 1926 and went on to become the champions of eleven playoffs, winning in 1936, 1937, 1943, 1950, 1952, 1954, 1955, 1997, 1998, 2002, and 2008. They proved themselves early on to have the ability to be a consistently good team, having continuously won cups for three straight decades in the 1930s-1950s, and then going on to do the same for two decades in the 1990s-2000s.

While they did suffer a 42-year drought between their times of glory, in which they were at the bottom of rankings and NHL betting odds, that’s now ancient history. They came back on top in the 90s, and they’ve remained there since. The Red Wings are now largely considered to be America’s most successful hockey franchise and boast great names such as Gordie Howe in addition to the title of being one of the NHL teams with the most Stanley Cup wins.

#2: Toronto Maple Leafs

1942 Toronto Maple Leafs Detroit Red Wings Stanley Cup final

In 1942 the Maple Leafs beat Detroit in the final

Since the NHL’s kick-off season way back in 1917, the Toronto Maple Leafs have won thirteen playoffs, including the inaugural 1918 Stanley Cup. From the 1910s-1960s, the Maple Leafs were an unstoppable force, winning an impressive number of Stanley Cups—including consecutive Cups—in 1922, 1932, 1942, 1945, 1947, 1948, 1949, 1951, 1962, 1963, 1964, and 1967.

Nowadays, the Maple Leafs fall short on rankings and in online casinos in the US. Coaches and rosters from the 1970s onwards have failed to bring the team back to its former glory. But the Maple Leafs shouldn’t be given up on yet—other teams have come back from decades-long playoff droughts, and it’s only a matter of time before the Maple Leafs get theirs and remind fans why they’re among the teams with the most Stanley Cup wins.

#1: Montreal Canadiens

Canadiens 1993 Stanley Cup victory

The last of Montreal”s numerous victories came in 1993

With an impressive twenty-three (or twenty-four, if you count one pre-NHL win) Stanley Cups underneath their belts and counting, it’s unlikely that the Montreal Canadiens will ever lose their position in history as the NHL team with the most Stanley Cup wins. Year-in and year-out since 1917, the Habs have proved themselves to be a French-Canadian powerhouse who deserve their top NHL betting picks position, having won in 1924, 1930, 1931, 1944, 1946, 1953, 1956, 1957, 1958, 1959, 1960, 1965, 1966, 1968, 1969, 1971, 1973, 1976, 1977, 1978, 1979, 1986, and 1993.

While they’re experiencing a small drought, it’s unlikely that it’ll last much longer. Even if they didn’t take home the Cup in the 2000s, and have to get one in the 2010s, they’ve remained playoff mainstays, and it’s only a matter of time before a Habs team captain will be hoisting the Stanley Cup overhead once again.

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