Teams With the Most Stanley Cup Championships

With their fourth Stanley Cup championship, the Pittsburgh Penguins expand the club of four-time winners or more, joining the Chicago Blackhawks, Boston Bruins, Montreal Canadiens, New York Islanders,Toronto Maple Leafs, Edmonton Oilers, New York Rangers and the Detroit Red Wings.

Pittsburgh Penguins – 4 Cups

2016 NHL Stanley Cup Final - Game Six

The Penguins entered the NHL in 1967, and have gone to the Stanley Cup Finals five times since, all since 1991. Mario Lemieux’s name is etched out over all the wins. He was the star player of the back-to-back feat in 1991 and 1992, and is the man who saved the franchise later, when he was no longer on the ice. Sidney Crosby has been the name most mentioned on the ice, leading the team to the title in 2009 and 2016, while also being on the losing side in 2008.

New York Rangers – 4 Cups

Rangers 1994 Stanley Cup

Part of the original six, the Rangers have played for the Cup 11 times, only winning it four. Their last trip that far was in 2014, losing to the Los Angeles Kings. It came after 20 years since their 1994 Stanley Cup victory, which broke a 54-year drought, which included 3 losses in the Cup Finals.

New York Islanders – 4 Cups

New York Islanders Stanley Cup

Founded in 1972, the Islanders formed one of the more dominant teams in North American sports history, winning the Cup four times in a row from 1980 to 1983, and losing in the Cup Finals a year later. Their run of 19 consecutive playoff series won remains unparalleled in the history of professional sports.

Edmonton Oilers – 5 Cups

Wayne Gretzky Stanley Cup

The Oilers have been in the NHL since 1979, and like the Islanders, are known for a brief (although longer) period of extreme dominance, with one name above it all: Wayne Gretzky. The Oilers won the Cup five times between 1984 and 1990, also making the final in 1983. They made it back there again in 2006, losing to the Carolina Hurricanes.

Chicago Blackhawks – 6 Cups

Blackhawks 2015 Stanley Cup

Another original six member, that has been moving up the rankings in recent years, winning the Stanley Cup in 2010, 2013 and 2015. The 2010 victory ended a 49 year wait, which included losses in five Cup finals series.

Boston Bruins – 6 Cups

Bruins 2011 Stanley Cup

The Bruins are tied for most losses in a Cup Finals series, losing 13 times out of their 19 visits. They ended 39 years of waiting in 2011 when they beat the Vancouver Canucks, and lost to the Blackhawks in 2013. Their golden age is considered to be the 70’s, when Bobby Orr skated the ice, winning the Cup in 1970 and 1972.

Detroit Red Wings – 11 Cups

Red Wings 2008 Stanley Cup

The Reds Wings have had a number of “golden eras”, but their most memorable one came in the mid 90’s and stretched into the new millennium, winning in 1997, 1998 and 2002. They played the Pittsburgh Penguins in both the 2008 and 2009 Cup finals, winning in 2008 and losing in 2009, to date their last trip to the finals.

Toronto Maple Leafs – 13 Cups

Maple Leafs 1967 Stanley Cup

A story that’s mostly tragic by now. The Maple Leafs have won the title 13 times, making the finals 21 times. However, they haven’t won it or been to the finals since 1967. In ’67, they won their fourth Stanley Cup of the 1960’s, in time when they felt invincible. Who knew it wouldn’t last, and the feeling wouldn’t come back for such a long time.

Montreal Canadiens – 24 Cups

Canadiens 1993 Stanley Cup

It’s been awhile since the Canadiens have won the Stanley Cup or been to the finals. Their last trip was in 1993, winning it, with Patrick Roy defending the goalposts. The Canadiens have more cups or finals (34) than any other NHL team, but it’s been 23 years since their last trip. That’s quite incredible, considering they went to the Cup Finals 11 times from 1965 to 1979, winning it 10 times.

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