How Much Do You Know About Stanley Cup Championship Teams?


By: John Miller

5 Min Quiz

Image: shutterstock

About This Quiz

The Stanley Cup Championship trophy is awarded to the winner of the National Hockey League playoffs. The trophy was first awarded in 1893 and is the oldest trophy currently still being awarded to a professional athletic team. The tournament takes place in an elimination-style that consists of four rounds, each made up of seven games. Based on points from the regular season, eight teams qualify from each of the two conferences. The finals pit the two conference champions against one another for the cup.

Notable champions include the Boston Bruins, who have won six Stanley Cup titles. The team was led by the greatest defenseman in the league’s history, Bobby Orr and Phil Esposito. Another notable team, winning a total of 24 titles, the Montreal Canadians have established themselves as the most prolific team to win the Stanley Cup.

How much do you really know about the Stanley Cup Championship and the teams that compete for the coveted trophy? Do you know who won the most Stanley Cups and who just had their first win? The only way to find out whether you are an expert in this field, or you still have a lot to learn, is to take this quiz!

Which team has won more Stanley Cups than any other?

Since the Stanley Cup era began in 1915, no team has been more successful than the Canadiens. They've won the title 24 times.


Which team has the second-most Cup appearances?

Like the Canadians, the Red Wings are NHL royalty. Detroit has made the Cup series 24 times since 1915.


Since 1915, the Canadiens have made how many Stanley Cup appearances?

The Canadiens are regular contenders for the Cup. Since 1915, they've made the title series 34 times … and won 24 of them.


True or false: Have the Detroit Red Wings won more Cup series than they've lost?

The Red Wings have come up short more times (13) than they've won (11). But their 24 appearances alone mean that Red Wings fans have no room to complain.


Of the following three teams, which has more Stanley Cup victories?

The Rangers are perennial contenders -- they've won the Cup four times. The Flames and Ducks both have one win each.


When was the last time the Canadiens won a Stanley Cup?

The Canadiens have far more titles than any other team … but they are in the middle of a terrible drought. They haven't snagged a Cup since 1993.


How many Cups do the Toronto Maple Leafs have to their credit?

Toronto used to be a regular powerhouse -- from 1918 to 1967, it won 13 Cups. But the Leafs haven't even made it to the Finals since '67.


Where would you find a Cup-winning team called the Penguins?

The Pittsburgh Penguins are one of modern hockey's most successful teams. They won the Cup in both 2016 and 2017, becoming the first back-to-back champs in nearly two decades.


Which team won four consecutive Stanley Cups in the '80s?

From '80 to '83, no one could touch the Islanders, who won four straight Cups. During that run, they won 19 consecutive playoff series, an incredible feat unmatched in any pro sport.


Which Cup-winning team is called the "Flyers"?

The Philadelphia Flyers have made eight Cup appearances in team history. And although they are regular contenders, they haven't won a Cup since 1975.


Which team has the most Finals appearances but has never claimed the Cup?

Vancouver fans have suffered their share of pain -- their Canucks have made the Finals three times -- most recently in 2011 -- but have never claimed a title.


Mario Lemieux was a star player who helped the _____ win their first-ever Cup.

Lemieux scored on the very first shot of his NHL career, a case of foreshadowing if we've ever seen one. In 1991, he went on to lead the Penguins to their first NHL title … and it would not be the last.


Since 2000, how many Cups have the Chicago Blackhawks won?

Chicago is one of the most venerated franchises in pro hockey. The club has six total Cups to its name, including three since the turn of the century.


Which team has two Cup titles and has never lost in the Finals?

The Avalanche joined the NHL in 1979 and they have a royal distinction, as they've won two Cups and never lost one. They are the only NHL team to win the Finals without having lost the series at least once.


Which pro team is the oldest continuously operating hockey club in the world?

The Montreal Canadiens were founded back in 1909, and they've been playing ever since, making them the oldest continuously operating pro hockey team in the entire world.


Where would you final an NHL team called the Devils?

The New Jersey Devils are serious rivals to the Flyers and Rangers. Since 2000, they've made the Finals four times. The team has three total Cups to its credit.


Guy Lafleur was a fantastic player who helped ______ win five Stanley Cups.

Lafleur was an instant star for the Montreal Canadiens starting back in the early '70s. As the first NHL player ever to score 50 goals and 100 points in six consecutive seasons, he helped the Canadiens win five Cups.


Which team is tied for the most Cup titles since the NHL-WHA merger?

Since the merger, Edmonton has won the Cup five times. That's a number equaled only by Pittsburgh.


When was the last time a Canadian team won the Stanley Cup?

For decades, Canadian teams had a stranglehold on the Cup … but the tide has turned. No Canadian team has won the Cup since 1993.


How many times have the Minnesota Wild made the Cup Finals?

The Wild have only been in the NHL for 16 seasons, and those years have been pretty lean. The Wild are one of just five active teams that have never made it to the Finals.


Which two teams are tied for the most Finals LOSSES?

Detroit and Boston have had their share of Finals glories … and defeats. Both teams have lost the Finals 13 times, more than any other NHL teams.


Which club is the first NHL team ever to win the Cup just a year after relocating to a new city?

The Colorado Avalanche used to be known as the Quebec Nordiques until they relocated to Denver after the '94-95 season. The team won the Cup that season, bringing immediate hockey glory to the Mile High city.


Which of the following teams has won the FEWEST Stanley Cups?

The Tampa Bay Lightning have two total title appearances, and they won one, in 2004. The team's second (unsuccessful) Cup appearance was in 2015.


How many teams have just one Finals appearance … and NO Cup victories?

Five teams have made just one appearance in the Finals, and none of them won the Cup. They are Ottawa, Florida, Nashville, Washington and San Jose.


Which of the following teams has the best Finals win percentage?

For a time, the Canadiens were ridiculously dominant. In 34 Finals appearances, they won 24 times, a .727 winning percentage.


Boston and Chicago are tied for Stanley Cup Finals wins. How many times have these teams won the Cup?

Boston and Chicago have illustrious Cup histories, as they've both won the title six times. But Boston needed six more Finals appearances than the Blackhawks to get to six wins.


Which American team did hockey great Wayne Gretzky join in 1988?

In 1988, the Kings completed a startling trade with Edmonton, bringing Gretzky to L.A. The star player not only drastically raised the status of hockey in the city but also helped the Kings win the Cup in 1993.


What is Pittburgh's Finals winning percentage?

Pittsburgh's fans must feel incredibly confident when the Penguins make the Finals. The team is 5-1 all-time (.833) in its Finals appearances.


The St. Louis Blues have appeared in three Cup Finals. How many have they won?

The Blues definitely have the blues. The team appeared in three consecutive Finals ('68-'70) but lost all of them … and they've never made it back to the title series.


Which team went 22 seasons without a playoff series victory, until finally breaking the trend in 2016?

The Islanders followed their dynasty years of the early '80s with an agonizing drought -- 22 straight seasons without a playoff series win. In 2016, they finally broke through and won again.


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