Fans of the game are quick to tell anyone who will listen that winning the NHL Stanley Cup is the most difficult professional trophy to win. And they have a point. Today, we take a look back at some of Stanley Cup’s finest moments, more memorable records, and then some random things we put in there to keep you on our toes. Some are easy, some challenging, and a few nearly impossible. All are pretty random.
Also Read: NFL Super Bowl Trivia Games Night
Good luck!
50 NHL Stanley Cup Trivia Questions and Answers
1. Who was the Stanley Cup named after?
Lord Frederick Arthur Stanley, the 16th Earl of Derby
2. What year was the Stanley Cup first awarded?
1893
3. Which team won the first Stanley Cup?
Montreal Hockey Club
4. What was the Stanley Cup originally called?
The Dominion Hockey Challenge Cup
5. Which team has won the most Stanley Cups?
Montreal Canadiens
6. How many Stanley Cups have the Montreal Canadiens won?
24
7. Which team has the second-most Stanley Cup wins?
Toronto Maple Leafs
8. Who is the only goaltender to have his name on the Cup as captain of a winning team?
Newsy Lalonde
9. Which team won the Stanley Cup in the 2023 season?
Vegas Golden Knights
10. Which team has never won a Stanley Cup as of 2025?
Seattle Kraken (among others)
11. Who was the first American team to win the Stanley Cup?
Seattle Metropolitans in 1917
12. What year did professional teams become eligible to compete for the Cup?
1906
13. Which team was the last non-NHL team to win the Stanley Cup?
Victoria Cougars in 1925
14. Which team lost in the Stanley Cup Final three years in a row since 1942?
St. Louis Blues
15. Who was the first player to win both Olympic gold and the Stanley Cup in the same year?
Ken Morrow
16. Which team holds the record for most consecutive Stanley Cup Final appearances?
Montreal Canadiens, with 10
17. Which team won four straight Stanley Cups from 1980 to 1983?
New York Islanders
18. Who is the only player to win the Conn Smythe Trophy as playoff MVP with two different teams?
Patrick Roy
19. Which coach has won the most Stanley Cups?
Scotty Bowman
20. What year was the best-of-seven Stanley Cup Final format introduced?
1939
21. Who scored the most goals in a single Stanley Cup Final series?
Jean Béliveau (record is 7 goals)
22. Which team won the Stanley Cup after sweeping all four rounds?
Detroit Red Wings in 1952
23. What is the oldest tradition involving the Stanley Cup?
Drinking champagne from the bowl
24. Which player has his name on the Cup the most times?
Henri Richard (11 times)
25. Who was the first coach to win five straight Stanley Cups?
Toe Blake
26. Which team won the Cup in 1994, ending a 54-year drought?
New York Rangers
27. Who was the first player to score a Stanley Cup-winning goal in overtime?
Pete Babando in 1950
28. Which team won the Cup in 2011?
Boston Bruins
29. Which team did the Detroit Red Wings defeat to win the Cup in 2002?
Carolina Hurricanes
30. Who was the first player to win the Conn Smythe Trophy on a losing team?
Roger Crozier
31. Who was the last player on a losing team to win the Conn Smythe?
Jean-Sebastien Giguere
32. What year was the Stanley Cup not awarded due to a pandemic?
1919 (Spanish flu)
33. What year was the Cup not awarded due to a lockout?
2005
34. Which team won the Cup in the 2020 “bubble” playoffs?
Tampa Bay Lightning
35. Who coached the Vancouver Canucks to the 1994 Stanley Cup Final?
Pat Quinn
36. Who coached the Mighty Ducks to the 2003 Final?
Mike Babcock
37. Who was the first player to win the Stanley Cup with three different teams?
Claude Lemieux
38. Which team won the Cup after the longest playoff run (most games)?
Los Angeles Kings in 2014 (26 games)
39. Which team won the Cup in 2018?
Washington Capitals
40. Who scored the Cup-winning goal for Chicago in 2010?
Patrick Kane
41. Which team won the most Cups in the 1970s?
Montreal Canadiens
42. Who was the first European captain to hoist the Cup?
Nicklas Lidstrom (Detroit Red Wings, 2008)
43. Which coach led the Penguins to their first Cup in 1991?
Bob Johnson
44. Who was the first team to win the Cup three years in a row more than once?
Montreal Canadiens
45. What is the largest margin of victory in a Stanley Cup game?
Ottawa Silver Seven, 21-0
46. Who was the first female to have her name on the Stanley Cup?
Marguerite Norris (Detroit Red Wings executive)
47. Which team won the Cup in 1999?
Dallas Stars
48. Who scored the “toe drag” goal in double overtime to win the 1996 Cup?
Uwe Krupp
49. What was the first year the Stanley Cup Final was broadcast live on TV?
1953
50. Who was the NHL commissioner as of 2010?
Gary Bettman
Unique Traditions and Anecdotes
Every player on the winning team gets to spend a day with the Cup, a tradition that has led to some unusual uses: from eating popcorn out of it (Martin Brodeur) to babies being baptized in its bowl.
The Cup has been accidentally dropped in a bonfire, left overnight in a canal, and even used as a flowerpot and a cereal bowl.
Red Kelly’s infant son once urinated in the Cup, and players have been known to drink from it shortly after.
Notable Stanley Cup Records
Most Wins: The Montreal Canadiens hold the record with 24 Stanley Cup victories, including an unmatched five consecutive championships from 1956 to 1960.
Most Consecutive Wins: Only the Canadiens (1956–1960), Canadiens again (1976–1979), and New York Islanders (1980–1983) have won four or more consecutive Cups.
Youngest Winner: Larry Hillman was just 18 years, 2 months, and 9 days old when he won with Detroit in 1955.
Oldest Winner: Chris Chelios was 46 years, 6 months old when he won with Detroit in 2008.
Most Times as a Player: Henri Richard has his name on the Cup 11 times as a player, more than anyone else.
Most as a Coach: Scotty Bowman has his name on the Cup nine times as a coach, spanning three franchises.
Unusual Occurrences
The Cup was not awarded in 1919 due to the Spanish flu pandemic and in 2005 due to the NHL lockout.
In 1962, the Toronto Maple Leafs dropped the Cup into a bonfire during a celebration, causing significant damage before it was repaired.
In 1905, Ottawa players kicked the Cup into the Rideau Canal during a drunken celebration and forgot it there overnight.
The New York Rangers’ 54-year championship drought (1940–1994) is often attributed to the “Curse of 1940,” after the team burned their arena’s mortgage in the Cup and allegedly urinated in it.
Random NHL Stanley Cup Fun Facts
There are actually three Stanley Cups: the original bowl, the authenticated “Presentation Cup” used today, and a replica displayed at the Hockey Hall of Fame.
The Cup weighs about 34 pounds and stands 35 inches tall, with rings added over the years to accommodate more names.
Only one eighth-seeded team has ever won the Cup: the 2012 Los Angeles Kings.
The Cup has been stolen, lost, and even used in strip club celebrations.
These stories and records make the Stanley Cup not just a symbol of hockey supremacy, but also a trophy with a colorful and storied legacy.
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