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NHL Playoff Trivia (Stanley Cup + Series History)

NHL playoff trivia covers the most dramatic moments in hockey: overtime goals, upset victories, dynasty runs, and Stanley Cup heroics. These questions test your knowledge of postseason history, from legendary Game 7s to controversial calls that changed championships.

January 24, 2026

Stanley Cup Champions & Dynasties

Q: Which team holds the record for most Stanley Cup championships? A: Montreal Canadiens with 24 Stanley Cups.

Q: Which team won four consecutive Stanley Cups from 1980 to 1983? A: New York Islanders.

Q: Which franchise became the first to win the Stanley Cup after joining the NHL via the WHA merger? A: The Edmonton Oilers in 1984.

Q: Which team is known for winning the Stanley Cup in 1994 to "end the 1940 chant"? A: The New York Rangers, who hadn't won since 1940.

Q: Which team won its first Stanley Cup in 2010, ending the league's longest active Cup drought at the time? A: The Chicago Blackhawks, who hadn't won since 1961.

Q: Which team has won the most Stanley Cups in the salary cap era (since 2005)? A: The Chicago Blackhawks and Pittsburgh Penguins are tied with three each.

Q: Which dynasty won five Stanley Cups in seven years during the 1950s? A: The Montreal Canadiens (1956-1960, five straight).

Q: Which team won back-to-back Cups in 2020 and 2021? A: The Tampa Bay Lightning.

Q: Which expansion team won the Cup in just its sixth season? A: The Philadelphia Flyers in 1974.

Q: Which team has appeared in the most Stanley Cup Finals without winning? A: The Vancouver Canucks with three Final appearances and no wins.

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Game 7 & Series Drama

Q: Game 7 of the 1979 semifinals between Montreal and Boston is remembered for what costly Boston penalty late in regulation? A: Too many men on the ice.

Q: Which team came back from a 3-0 series deficit to beat the Boston Bruins in 2010? A: The Philadelphia Flyers.

Q: How many times has a team come back from a 3-0 series deficit to win in NHL playoff history? A: Four times, most recently the Los Angeles Kings over San Jose in 2014.

Q: Which goalie is famous for backstopping the New Jersey Devils to three Stanley Cups in 1995, 2000 and 2003? A: Martin Brodeur.

Q: Which team lost the Stanley Cup Final on a controversial crease-rule goal in 1999? A: The Buffalo Sabres. Brett Hull's Cup-winning goal for Dallas appeared to have his skate in the crease.

Q: Which team blew a 3-1 series lead in the 1942 Stanley Cup Final? A: The Detroit Red Wings lost to Toronto in what remains the only 3-0 comeback in Cup Final history.

Q: Which team came back from 3-1 down to beat Pittsburgh in the 2021 first round? A: The New York Islanders.

Q: What is the record for most Game 7s played in a single playoff run? A: Three Game 7s, accomplished by several teams including the 2011 Boston Bruins.

Q: Which team won three Game 7s in a row en route to the 2019 Stanley Cup? A: The St. Louis Blues.

Q: Which goalie has the most career Game 7 wins? A: Patrick Roy with 14 Game 7 wins.

Overtime & Iconic Goals

Q: Who scored the 1970 Stanley Cup-winning overtime goal while flying through the air? A: Bobby Orr of the Boston Bruins against St. Louis.

Q: Which player scored the series-clinching goal in double overtime of Game 7 for the Toronto Maple Leafs in 1993 against Detroit? A: Nikolai Borschevsky.

Q: Whose triple-overtime goal in 2000 won Game 6 and the Stanley Cup for the New Jersey Devils? A: Jason Arnott against the Dallas Stars.

Q: Which player scored the Game 6 overtime goal in 2010 that clinched the Stanley Cup for Chicago? A: Patrick Kane in the famous goal that went in so quickly few people initially saw it.

Q: Which Detroit Red Wings forward is remembered for a dramatic Game 7 overtime goal in the 1997 playoffs? A: Darren McCarty's goal against Colorado is one of the most famous in Red Wings history.

Q: Which player scored in multiple overtime periods in the 2013 playoffs for Boston? A: Patrice Bergeron had several overtime goals during the Bruins' Cup run.

Q: What is the longest Game 7 in NHL history by time? A: Several Game 7s have gone to multiple overtimes, with some lasting over 100 minutes of play.

Q: Which player scored the series-winning overtime goal for Washington in 2018 to send them to their first Cup Final? A: Devante Smith-Pelly or another Capitals player (adjust based on specific moment preferred).

Q: Which goalie made "The Save" in 1994 for the Rangers? A: Mike Richter's famous save against Pavel Bure in Game 4 of the Finals.

Q: Who scored the Cup-clinching goal for Pittsburgh in 2009? A: Maxime Talbot with two goals in Game 7 against Detroit.

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Upsets, Curses & Oddities

Q: Which 8-seed swept the top-seeded Montreal Canadiens in 2010? A: The Philadelphia Flyers in the Eastern Conference Semifinals.

Q: Which Canadian franchise reached the Cup Final in 2011 but lost in seven games, sparking riots downtown? A: Vancouver Canucks.

Q: Which expansion team made the Stanley Cup Final in its first season, in 2018? A: The Vegas Golden Knights.

Q: Which Southern US team beat the Detroit Red Wings in the 1996 playoffs, then memorably threw plastic rats on the ice? A: The Florida Panthers. The "rat trick" became their playoff tradition.

Q: Which team's post-1967 playoff struggles are often described as a "curse" by its own fan base? A: The Toronto Maple Leafs, who haven't won a Cup since 1967.

Q: Which team was the lowest seed to ever win the Stanley Cup? A: The Los Angeles Kings won as an 8-seed in 2012.

Q: Which team came within one win of the Cup in 2004 before losing Game 7 at home? A: The Calgary Flames lost to Tampa Bay.

Q: Which goalie's playoff performance in 2006 led the underdog Oilers to Game 7 of the Finals? A: Dwayne Roloson, until he was injured and replaced by Ty Conklin.

Q: Which team blew a 3-0 lead late in Game 7 to lose the series in 2014? A: The San Jose Sharks against the Los Angeles Kings in an all-time collapse.

Q: Which Cinderella team made the Cup Final in 2021 despite being heavy underdogs? A: The Montreal Canadiens surprised everyone by reaching the Final.

Why Playoff Trivia Hits Different

Playoff moments carry more weight than regular season achievements. Overtime goals, Game 7 heroics, and upset victories become part of hockey lore because the stakes are highest when everything's on the line. Knowing playoff history means understanding what truly matters in hockey.

The Drama That Defines Playoff Hockey

Playoff hockey delivers drama no other sport can match. Overtime periods that stretch past midnight, goalies standing on their heads, role players becoming heroes. These moments create the stories fans tell for decades, which is why playoff trivia resonates more deeply than regular season stats.

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