Toronto Maple Leafs Trivia
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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 01Toronto's NHL champions of 1917-18, the league's first season, are in the record books under what name?
Arenas
Arenas is the name in the record books, after the Arena Company that ran the club; at the time press and fans also called it the Blueshirts or simply the Torontos.
Q 02Before Conn Smythe made them the blue-and-white Maple Leafs in 1927, Toronto's NHL team wore which colour?
Green
Green came with the name: the owners of 1919 called the team the St. Patricks, hoping to draw Toronto's large Irish population to its games.
Q 03Conn Smythe's group bought the St. Patricks in 1927, beating a rival who wanted to move the team where?
Philadelphia
Philadelphia was where a rival bidder meant to take the team with his $200,000 offer; Smythe's group won with $160,000 and an appeal to civic pride.
Q 04Conn Smythe said he chose the maple leaf because of his experience as what?
A First World War soldier
A First World War soldier, later shot down and held prisoner, Smythe called the maple leaf a badge of courage; a Toronto baseball club had already carried the name for more than thirty years.
Q 05The Leafs say the blue in their colours stands for Canadian skies and the white for what?
Snow
Snow is the club's answer, though Conn Smythe's sand-and-gravel trucks wore the same blue and white, as did the University of Toronto teams he had played for and coached.
Q 06Maple Leaf Gardens was built in 1931 on land bought from which Toronto retailing family?
Eaton
Eaton's sold the site for $350,000, a price said to be well below market value, and the arena rose on it in five months in the depths of the Depression.
Q 07The radio broadcaster's press box high above the Gardens ice was nicknamed what?
The gondola
The gondola hung over the Gardens ice for 48 years, until 1979, when the Leafs' owner had it torn out and burned to make room for private boxes.
Q 08The Leafs' 1930s 'Kid Line' featured Busher Jackson, Joe Primeau and whom?
Charlie Conacher
Charlie Conacher, the line's right winger with the booming shot, twice won the NHL scoring title; the three 'kids' took the 1932 Stanley Cup and then lost final after final.
Q 09Whose No. 6, retired in 1934 after an Eddie Shore hit, was pro sports' first retired number?
Ace Bailey
Ace Bailey received the proceeds of a benefit game between the Leafs and a team of NHL all-stars; before it, he shook hands with Shore, the man who had ended his career.
Q 10The 1942 Leafs remain, as of 2026, the only team to do what in a Stanley Cup Final?
Win after trailing 3-0
Win after trailing 3-0: with Detroit one victory away, coach Hap Day benched scoring star Gordie Drillon for seldom-used Don Metz, and Toronto took the next four games.
Q 11Bill Barilko, whose plane vanished in northern Ontario months after his 1951 Cup-winning goal, came from which mining town?
Timmins
Timmins lost its hero on a fishing-trip flight; the wreck lay hidden for eleven years and was found weeks after the Leafs' next Cup win in 1962, a tale told in The Tragically Hip's 'Fifty Mission Cap'.
Q 12Every game of the 1951 Toronto–Montreal Cup Final featured what?
Overtime
Overtime decided all five games: the last ended when defenceman Bill Barilko left his post, against his coach's orders, and scored the goal that won the Cup.
Q 13The Leafs' 1967 Stanley Cup, their 13th, was won in six games over which team?
Montreal Canadiens
Q 21After a decade sitting vacant, Maple Leaf Gardens reopened in 2011 with what occupying its lower floors?
A Loblaws supermarket
A Loblaws supermarket opened on the ground floor in November 2011; a university rink was then built on the top level, so hockey is still played under the old roof.
Q 22The Leafs' polar bear mascot wears No. 60 and is named after which Toronto street?
Carlton Street
Carlton Street, where Maple Leaf Gardens stood at No. 60, gave the bear both his name and his number when he arrived in 1995, four years before the team moved to Bay Street.
Q 23The Leafs lost the 2002 conference finals to which 'Cinderella' team?
Carolina Hurricanes
Montreal Canadiens had won the last two Cups and planned to show off the next at Expo 67 in their own city; a much older Toronto team spoiled the plan.
Q 14Which Leafs defenceman scored the Game 6 winner in the 1964 Final on a broken ankle?
Bob Baun
Bob Baun was carried off after stopping a Gordie Howe shot, had the ankle frozen, came back and scored the winner; Toronto then won Game 7 for a third straight Cup.
Q 15Which Leafs owner was jailed for fraud and theft in 1972 and still kept the club?
Harold Ballard
Harold Ballard had only just bought control when he was jailed; his partner Stafford Smythe, charged alongside him, died shortly before his own case reached court.
Q 16Which Leafs captain had six goals and four assists against Boston on 7 February 1976, an NHL single-game points record?
Darryl Sittler
Darryl Sittler's ten points beat a record of eight that had stood since 1944; every one came against rookie goalie Dave Reece, who never played in the NHL again.
Q 17A Leafs captain cut the C off his sweater in 1979 in a feud with which GM?
Punch Imlach
Punch Imlach, back after winning four Cups in the 1960s, could not trade a captain with a no-trade contract, so he traded the captain's closest friends instead, Lanny McDonald among them.
Q 18Which Kings star high-sticked Doug Gilmour unpenalised in the 1993 conference final, then scored the winner?
Wayne Gretzky
Wayne Gretzky's stick cut Gilmour in Game 6, no penalty was called and he scored moments later; Toronto, one win from a Cup Final against Montreal, lost the series in seven.
Q 19A 1994 draft-day trade that sent the Leafs' captain to Quebec brought which future captain to Toronto?
Mats Sundin
Mats Sundin had been the first European drafted first overall; in 1997 he became the Leafs' first non-Canadian captain, and in 2026 he came back as a senior adviser in the front office.
Q 20The Leafs left Maple Leaf Gardens in February 1999 for a new arena that opened under what name?
Air Canada Centre
Air Canada Centre kept that name until 2018, when it became Scotiabank Arena; the Gardens farewell was a loss to Chicago, the same team that had beaten the Leafs there on opening night in 1931.
Carolina Hurricanes reached their first Stanley Cup Final when Martin Gelinas scored the Game 6 winner, minutes after Toronto's captain had tied it with seconds left.
Q 24Whose three shutouts carried the Leafs past Ottawa in the first round in 2004?
Ed Belfour
Ed Belfour blanked Ottawa three times in the seven games, as Toronto knocked the Senators out of the playoffs for the fourth time in five springs.
Q 25In 2009 Brian Burke traded two first-round picks and a second to Boston for which winger?
Phil Kessel
Phil Kessel cost the first-round picks that Boston used on Tyler Seguin and Dougie Hamilton; six years later the rebuilding Leafs traded him on to Pittsburgh.
Q 26Which president began a 'scorched earth' Leafs rebuild in 2015 and left in 2025?
Brendan Shanahan
Brendan Shanahan's teardown ended in a last-place finish and the lottery win that brought Auston Matthews; the club let him go after another playoff defeat in 2025.
Q 27In his 2016 NHL debut, Auston Matthews became the first player of the modern era to do what?
Score four goals
Score four goals he did, against Ottawa, and Toronto still lost in overtime; he finished the season with the Calder Trophy as the league's best rookie.
Q 28Whose Leafs record of 54 goals did Auston Matthews break in 2022?
Rick Vaive
Rick Vaive, the first Leaf to score 50 in a season, held the record for forty years; he also lost the captaincy in 1986 after sleeping through a morning practice.
Q 29Auston Matthews grew up in which Arizona city, attending Coyotes games from age two?
Scottsdale
Scottsdale is no hockey heartland, and his route stayed unusual: instead of junior or college hockey, he spent his draft year playing as a professional in Zurich.
Q 30The Leafs signed which centre to a seven-year, $77 million deal in 2018 and named him captain in 2019?
John Tavares
John Tavares called signing with his boyhood team a childhood dream; he wore the C for five seasons before handing it to Auston Matthews in 2024.