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50 free Toronto Maple Leafs trivia questions with answers — sports quiz, new questions added Aug 2026.
This Toronto Maple Leafs trivia quiz starts with the Arenas and St. Patricks, Conn Smythe's $160,000 purchase and the maple leaf he saw as a badge of courage, Foster Hewitt's gondola, the Kid Line and Ace Bailey, the 1942 reverse sweep, Bill Barilko's goal and disappearance, Punch Imlach's 1960s dynasty and the 1967 Cup, then the long drought: Harold Ballard's prison term, Darryl Sittler's 10-point night, Doug Gilmour and Kerry Fraser's missed call, Mats Sundin's captaincy, the Bruins collapses and the Auston Matthews era with a 69-goal season, Mitch Marner's exit and Gavin McKenna at first overall. The buildings and identity get their own round: Mutual Street Arena, Maple Leaf Gardens and its Loblaws afterlife, Air Canada Centre, Carlton the Bear's number, blue for the sky and white for snow, and the first retired number in pro sports. Easy questions suit any Leafs fan; the hard ones are for people who know how many charges Ballard was convicted on. Every answer has been checked against an encyclopaedic source and each question shows its citation once you have answered.
30 of 50 questions with answers and explanations. Play the quiz
Q 01The franchise began play in the NHL's first season, 1917-18, under what name?
Arenas
The team won the Stanley Cup that first season, though the Leafs do not count the earlier Blueshirts' history as their own.
Q 02The Toronto St. Patricks wore what colour from 1919 until Conn Smythe took over?
Green
Babe Dye scored four in the 1922 Cup clincher over the Vancouver Millionaires under the St. Pats banner.
Q 03Conn Smythe's group bought the St. Patricks in 1927, beating a rival who wanted to move the team where?
Philadelphia
C. C. Pyle had offered $200,000; Smythe argued civic pride mattered more than money.
Q 04Conn Smythe said he chose the maple leaf as a logo because of his experience as what?
A First World War officer and prisoner of war
He called it a badge of courage worn by Canadian soldiers; a Toronto baseball club had used the name since 1895.
Q 05Conn Smythe said the Leafs' colours meant sky and snow, but they also matched what?
The trucks of his gravel and sand business
Blue had long been associated with Toronto teams, going back to the Argonaut Rowing Club.
Q 06Maple Leaf Gardens was built in 1931 on land bought from which Toronto retailing family?
Eaton
Construction took five months, and the Leafs lost the opener 2-1 to Chicago on November 12, 1931.
Q 07The radio broadcaster's press box high above the Gardens ice was nicknamed what?
The gondola
A General Motors ad man said it looked like the gondola of an airship.
Q 08The Leafs' 1930s 'Kid Line' featured Busher Jackson, Joe Primeau and whom?
Charlie Conacher
Coached by Dick Irvin, they won the 1932 Cup over the Rangers, whom Smythe had been fired by before ever coaching a game.
Q 09Whose No. 6, retired in 1934 after an Eddie Shore hit, was pro sports' first retired number?
Ace Bailey
The Ace Bailey Benefit Game held to pay his medical bills was the NHL's first All-Star Game.
Q 10The Leafs remain the only team to do what in a Stanley Cup Final, against Detroit in 1942?
Come back from 3-0 down to win
Fourth-liner Don Metz sparked the reverse sweep, and Conn Smythe arrived at Game 7 in full military uniform.
Q 11Bill Barilko vanished in a 1951 plane crash near which Ontario town, months after his Cup-winning goal?
Timmins
The wreck was found in 1962, the same spring the Leafs next won the Cup; his No. 5 was retired in 1992.
Q 12How many games of the 1951 Toronto–Montreal Stanley Cup Final went to overtime?
All five
Barilko left his defensive post against orders to score the winner in Game 5.
Q 13The Leafs' 1967 Stanley Cup, their 13th, was won in six games over which team?
Montreal Canadiens
Jim Pappin scored the series winner; by 2025 the drought that followed had stretched to 57 seasons, the longest in league history.
Q 21After a decade sitting vacant, Maple Leaf Gardens reopened in 2012 with what occupying its lower floors?
A Loblaws supermarket
Toronto Metropolitan University's arena, the Mattamy Athletic Centre, sits on the top level.
Q 22The Leafs' polar bear mascot wears No. 60 for what reason?
The Gardens' street address was No. 60
The polar bear made his first public appearance on July 29, 1995.
Q 23The Leafs lost the 2002 conference finals to which 'Cinderella' team?
Carolina Hurricanes
Q 14Which coach-GM led the Leafs to four 1960s Cups and holds the club record for games coached?
Punch Imlach
He coached 770 regular-season games for Toronto and later spun the Buffalo Sabres' lucky wheel.
Q 15In 1972 majority owner Harold Ballard was convicted on how many charges of fraud and theft?
47
He served time at Millhaven and later said prison was like a motel with colour TV, golf and steak.
Q 16Darryl Sittler set the NHL single-game record with 10 points on February 7, 1976, against which team?
Boston Bruins
All six goals and four assists came against rookie goalie Dave Reece in an 11-4 win.
Q 17Darryl Sittler relinquished the Leafs captaincy in a dispute with which returning GM?
Punch Imlach
Imlach traded Sittler's friend Lanny McDonald partly to undermine him.
Q 18Which Kings star high-sticked Doug Gilmour unpenalised in the 1993 conference final, then scored the winner?
Wayne Gretzky
Toronto had led the series 3-2 and dreamed of a Cup Final against Montreal.
Q 19The 1994 draft-day trade that sent Wendel Clark to Quebec brought which future captain to Toronto?
Mats Sundin
In 1997 he became the first non-Canadian to captain the Leafs, and no European-born player has captained an NHL team longer.
Q 20The Leafs played their last game at Maple Leaf Gardens in February 1999 before moving to which arena?
Air Canada Centre
The building was renamed Scotiabank Arena in 2018 and holds 18,819 for Leafs games.
Toronto had needed seven games each to get past the Islanders and Senators.
Q 24Whose three shutouts carried the Leafs past Ottawa in the first round in 2004?
Ed Belfour
He had replaced Curtis Joseph in 2002 and was a Vezina finalist his first year in Toronto.
Q 25In 2009 Brian Burke traded two first-round picks and a second to Boston for which winger?
Phil Kessel
The picks became Tyler Seguin and Dougie Hamilton; Phaneuf arrived from Calgary months later.
Q 26Which president began a 'scorched earth' Leafs rebuild in 2015 and left in 2025?
Brendan Shanahan
The rebuild bottomed out with a last-place finish and the lottery win that delivered Auston Matthews.
Q 27Auston Matthews became the first player in modern NHL history to do what in his debut in 2016?
Score four goals
The Leafs still lost the game to Ottawa in overtime.
Q 28Auston Matthews set the Leafs' single-season record in 2023-24 with how many goals?
69
It brought him his third Rocket Richard Trophy; he had been the first Leaf ever to win it, in 2021.
Q 29Auston Matthews grew up in which Arizona city, attending Coyotes games from age two?
Scottsdale
He was born in San Ramon, California, and played a year in Zurich before the 2016 draft.
Q 30The Leafs signed which centre to a seven-year, $77 million deal in 2018 and named him captain in 2019?
John Tavares
He was the club's 25th captain; the job later passed to Matthews.