The NHL is without a doubt the most popular ice hockey league in the world, and the team who wins it all each season gets to take home the Stanley Cup.

There are many ways to judge which team is best, besides who takes home the hardware.

You could judge them by the NHL Finals odds. You could judge them by their fanbase. Or, you could judge them by their successful players.

However, the most common way that people will judge a team is by how many championships they have won.

There are seven teams in the NHL who have won the Stanley Cup five times or more, and we will look at each of these teams, so you know who is the best of the best.

#1: The Montreal Canadiens

The team that has the most Stanley Cups is the Montreal Canadiens. They have been in the NHL for 104 years, and in that time, they have taken home 24 Stanley Cups.

With 24 titles in their 104 seasons, this gives them a success rate of over 20%.

They were founded in 1909, which also makes them the oldest team in the modern-day NHL.

The Canadiens have actually been around so long and have had such success that many other fanbases hate them. Boston Bruins’ fans hate them the most of all, but it’s not like they are going to catch up to the team’s impressive 24 Cups soon, anyway.

The Canadiens managed to win in 1916, 1924 1930, 1931, 1944, 1946, 1953, 1956, 1957, 1958, 1959, 1960, 1965, 1966, 1968, 1969, 1971, 1973, 1976, 1977, 1978, 1979, 1986 and 1993.

They made the Stanley Cup in 2021, but lost to the Tampa Bay Lightning in five games.

#2: The Toronto Maple Leafs

The team with the second-highest number of Stanley Cup wins is the Toronto Maple Leafs. Also in the NHL for 104 years, they have won 13 Stanley Cups.

The Maple Leafs are not quite at the level of the Canadiens. Nonetheless, they have still managed to grab 13 Stanley Cups in their 104 years. However, much like the Canadiens, all of their wins came before the turn of the 21st century.

The Leafs won their Stanley Cups in 1918, 1922, 1932, 1942, 1945, 1947, 1948, 1949, 1951, 1962, 1963, 1964 and 1967.

It has been almost 60 years since the Maple Leafs won a Stanley Cup.

#3: Detroit Red Wings

The team with the third-highest number of Stanley Cups is the Detroit Red Wings. They have been in the NHL for 95 years and have won 11 Stanley Cups.

The Red Wings only have two fewer Stanley Cups than the Maple Leafs, but have been around for nine years less.

They won the Stanley Cup in 1936, 1937, 1943, 1950, 1952, 1954, 1955, 1997, 1998, 2002 and 2008.

This makes them the first team on our list to have won a Stanley Cup after the year 2000.

#4: Boston Bruins/ Chicago Blackhawks

The Bruins and Blackhawks are tied for fourth. The Bruins have been in the NHL for 97 years and the Blackhawks have been in the NHL for 95 years.

Both have six Stanley Cups.

The Boston Bruins have won six times — in 1929, 1939, 1941, 1970, 1972 and 2011 — whereas the Blackhawks won in 1934, 1938 1961, 2010, 2013 and 2015.

#5: Edmonton Oilers/Pittsburgh Penguins

The Oilers and the Penguins round out the top-five. The Oilers have been in the NHL for 42 years and the Penguins have been around for 54 years.

Both teams have won five Stanley Cups each.

The Oilers won Stanley Cups in 1984, 1985, 1987, 1988 and 1990. The Penguins have won five Cups after 1990 — in 1991, 1992, 2009, 2016, and 2017.

John Smark