Toronto Maple Leafs Trivia – From Easy to Impossible

It’s time to see how well you know the Toronto Maple Leafs with this progressively more difficult game of trivia all about the team and its history.

Gather your friends and prepare for a quiz to test your knowledge about the Original Six team that has the best fans on the planet. Emerce yourself in Toronto Maple Leafs trivia.

The quiz is broken into four different levels. It begins with easy, moves to medium, then hard, and finishes with impossible level questions.

Not only can you gain bragging rights by getting questions right but you are recommended to spend time with the answer to each question to learn more about the Leafs.

Easy Level Questions

1. Where was Mats Sundin Born?

a) Finland
b) Sweden
c) Canada
d) Estonia

2. Other than Auston Matthews, who was Toronto’s only first overall NHL Draft pick?

a) Wendel Clark
b) Lanny McDonald
c) Gary Nylund
d) Russ Courtnall

3. A Maple Leafs player owns the record for most points in a single game with ten. Who accomplished the feat?

a) Darryl Sittler
b) Dave Keon
c) Auston Matthews
d) John Tavares

4. Toronto Maple Leafs owner Harold Ballard once asked Roger Neilson to coach wearing what over his head?

a) A Christmas wreath
b) A ski mask
c) A paper bag
d) A Frankenstein mask

5. Mats Sundin was drafted first overall by which team?

a) Hartford Wailers
b) Atlanta Thrashers
c) Quebec Nordiques
d) Toronto Maple Leafs

6. How many arenas were home to the Toronto Maple Leafs?

a) 1
b) 2
c) 3
d) 4

7. Which nickname doesn’t match the player?

a) Cecil Henry “Babe” Dye
b) Leonard Patrick “Red” Kelly
c) David James “Tiger” Williams
d) George “Patch” Imlach

8. Which organization once owned the Toronto Maple Leafs?

a) Elementary Teachers Federation of Ontario (ETFO)
b) Ontario Teachers Insurance Plan (OTIP)
c) Ontario College of Teachers (OCT)
d) Ontario Teachers Pension Plan (OTPP)

10. What’s the Maple Leafs’ mascot name?

a) Garden Bear
b) Smokey the Bear
c) Blue the Bear
d) Carlton the Bear

Interesting Defenceman Trivial Factoids

• Maple Leafs player Borje Salming was the first NHL defenceman trained in Europe to get 500 points in the league. He was inducted into the Hockey Hall of Fame in 1996.
• Despite having had many excellent defencemen, no Maple Leafs player has ever won a Norris Trophy.
• Rasmus Sandin has a brother who plays pro hockey. He plays in the Swedish Elite League.
• When Luke Schenn was playing minor hockey for the Saskatoon Red Wings he was coached by his father Jeff
• Even though Maple Leafs defenceman Bryan Berard suffered a serious slash to his eye’s sclera he managed to play six more seasons in the NHL. His retina was torn his retina detached when Marian Hossa’s stick stuck Berard in his right eye. Doctors initially believed he’d lose his eye.

Easy Level Answers

1. Where was Mats Sundin Born?

A: b) Sweden
Mats Sundin was born on Feb 13, 1971, in Bromma, Sweden

2. Other than Auston Matthews, who was Toronto’s only first overall NHL Draft pick?

A: a) Wendel Clark
Wendel Clark was the first overall pick in 1985. Russ Courtnall went seventh in the 1983 draft, while Gary Nylund went third overall a year earlier. Lanny McDonald was the fourth player chosen in the 1973 draft.

3. A Maple Leafs player owns the record for most points in a single game with ten. Who accomplished the feat?

A: a) Darryl Sittler
On Feb. 7, 1976, Darryl Sittler had the best game of his career. He helped the Leafs beat the Boston Bruins with his six goals and four assists. The second most points in a game was eight, which was accomplished by Rocket Richard. He had five goals and three assists.

4.  Maple Leafs owner Harold Ballard once asked Roger Neilson to coach wearing what over his head?

A: c) A paper bag
Harold Ballard fired Roger Neilson partway through the 1978-79 season. After some backlash, Ballard gave Neilson his job back. He wanted the coach to wear a paper bag over his head for his first game back behind the bench. Neilson refused to do it and Ballard fired him for a second time at the end of that season.

5. Mats Sundin was drafted first overall by which team?

A: c) Quebec Nordiques
In the 1989 NHL Entry Draft, Sundin was selected by the Quebec Nordiques first overall.

6. How many arenas were home to the Toronto Maple Leafs?

A: c) 3
The first arena to host the Maple Leafs was known by three different names. It was just called Arena or Arena Gardens. It was also renamed Mutal Street Arena later before eventually being converted to a curling club and roller skating rink and given its final name, Mutual Street Arena.

The next rink was known as the “cathedral” of hockey, Maple Leaf Gardens. The Leafs played their final game there in 1999 before they moved to their current home on Bremner Blvd, the Air Canada Centre, which was renamed Scotiabank Arena.

7. Which nickname doesn’t match the player?

A: d) George “Patch” Imlach
George Imlach is more widely known as “Punch”. He was not just one of the Leafs’ five best general managers but he was also one of the team’s five best coaches.

8. Which organization once owned the Toronto Maple Leafs?

A: d) Ontario Teachers Pension Plan (OTPP)
OTPP became the majority stakeholder of the Maple Leafs from Steve Stavro in 1994. They grew the company until selling it for $1.32-billion in 2012. Forbes named it “the greatest sports deal in history“. That’s because it took 18 years to turn their initial $50 million for a 49% stake into $1.32 billion.

9. In what year did the Maple Leafs win their last Stanley Cup?

A: b) 1967
The Toronto Maple Leafs have won 13 championships. They won cups in 1918, 1922, 1932, 1942, 1945, 1947, 1948, 1949, 1951, 1962, 1963, 1964, and 1967.

10. What’s the Maple Leafs’ mascot name?

A: d) Carlton the Bear
The official mascot of the Maple Leafs is Carlton the Bear. He got his name when the team played at Maple Leafs Gardens. That arena was located on Carlton Street.

Medium Level Questions

1. Which of the following players was never a Toronto Maple Leafs captain?

a) Tim Horton
b) Rob Ramage
c) Sid Smith
d) Charlie Conacher

2. Who had the most shutouts as a member of the Toronto Maple Leafs?

a) Johnny Bower
b) Turk Broda
c) Harry Lumley
d) Mike Palmateer

3. What was the first team name of the Toronto Maple Leafs organization?

a) Toronto Blueshirts
b) Toronto Arenas
c) Toronto Huskies
d) Toronto St. Patricks

4. Who has played the most games with the Toronto Maple Leafs?

a) Allan Stanley
b) Doug Gilmour
c) George Armstrong
d) Tie Domi

5. What’s true about Harold Ballard, the Leafs’ majority owner from 1972-1990?

a) He had ten children
b) He owned and flew three personal blimps
c) He ran two soup kitchens and volunteered at both every Sunday
d) He spent three years in prison

6. Which Leafs GM traded Tuukka Rask to Boston for Andrew Raycroft?

a)  John Ferguson Jr.
b) Brian Burke
c) Cliff Fletcher
d) Dave Nonis

7. Who was Phil Kessel’s roommate in Toronto?

a) Colby Armstrong
b) Tomas Kaberle
c) Tyler Bozak
d) Joffrey Lupul

Interesting Coaching Trivial Factoids

• Roger Neilson who started his NHL coaching career with the Leafs is the only person to coach eight teams in the league.
• Dick Irvin owns the record for consecutive years coaching in the NHL. He did the job for 26 years. Irvin spent nine of those seasons behind the Leafs bench.
• Two Maple Leafs coaches share the record for the shortest tenure as the team’s head coach. Both Dick Duff and Mike Rodden (St. Patricks) each had the role for a total of two games.
• Pat Burns won the most Jack Adams Awards. He had three in total, one of them with the Maple Leafs for his efforts in the 1992-93 season.
• There have only been two people to ever coach a Memorial Cup championship team the same year they played in the NHL. They are Hap Day and Billy Reay. Day coached the OHA Toronto West End Nationals who won the cup in 1936. He was also playing as a defenceman with the Leafs at the time.

Medium Level Answers

1. Which of the following players was never a Toronto Maple Leafs captain?

A: a) Tim Horton
Sid Smith and Charlie Conacher were captains of the team for a single season each. Rob Ramage held the role for two years just before it was taken over by Wendel Clark. Even though Tim Horton had an incredible career, he was never a Leafs captain.

2. Who had the most shutouts as a member of the Toronto Maple Leafs?

A: b) Turk Broda
Each of the four goalies listed were excellent for the Leafs. Mike Palmateer ranks ninth on the Leafs all-time shutout list with 15. Johnny Bower had 32, good enough for third. Harry Lumley was second with 34 and Turk Broda had far more than anyone else with 61 shutouts.

3. What was the first team name of the Toronto Maple Leafs organization?

A: a) Toronto Blueshirts
The Toronto Blueshirts were founded in 1911 and began to play in 1912. It began as the first Toronto team in the National Hockey Association (NHA). It won its only Stanley Cup in 1914. It ran until 1917 when the team’s name was changed to the Toronto Arenas or Torontos. The name was changed once again in 1919 to the Toronto St Pats. In 1927 the team became the Maple Leafs, a name that clearly has stuck.

The Blueshirts weren’t the first professional hockey team to play in Toronto. That distinction belongs to the Toronto Professional Hockey Club. They played in the Ontario Professional Hockey League (OPHL) from 1906-09.

4. Who has played the most games with the Toronto Maple Leafs?

A: c) George Armstrong
George Armstrong had more games played by a wide margin than any other players in the multiple-choice. However, he didn’t play many more games than the runner-up in this statistical category.

5. What’s true about Harold Ballard, the Leafs’ majority owner from 1972-1990?

A: d) He spent three years in prison
Ballard wasn’t the most honest person to ever be associated with the team. In fact, he was convicted on 47 fraud charges. This resulted in him serving three years in prison.

6. Which Leafs GM traded Tuukka Rask to Boston for Andrew Raycroft?

A: a)  John Ferguson Jr.
In what has widely been considered the worst trade in franchise history, JFJ chose to ship one of their two top goaltending prospects to the Bruins. The Leafs gambled on a declining Andrew Raycroft and that Justin Pogge would develop into a stud.

7. Who was Phil Kessel’s roommate in Toronto?

A: c) Tyler Bozak
Phil Kessel was known to be a reticent person but stories of him sharing an apartment with Tyler Bozak flooded the media. The duo even gave a tour to the camera for a Road to the Winter Classic special.

Hard Level Questions

1. Who was the youngest player to captain the Toronto Maple Leafs?

a) Hap Day
b) Syl Apps
c) Ted Kennedy
d) Rick Vaive
e) Dion Phaneuf

2. Which legendary player scored their last Stanley Cup Playoffs goal against the Toronto Maple Leafs?

a) Wayne Gretzky
b) Gordie Howe
c) Maurice Richard
d) Mario Lemieux

3. True or False: The Toronto Maple Leafs are the only Original Six team to finish the season in fourth place and win the Stanley Cup

a) True
b) False

4. Robert Reichel put the puck in his own net to give which Sabres goaltender an NHL goal?

a) Ryan Miller
b) Martin Biron
c) Bob Essensa
d) Mika Noronen

5. Who is the only Toronto Maple Leafs Player to wear #99 on his sweater?

a) Kris Newbury
b) Wilf Paiement
c) Nathan Dempsey
d) Al Iafrate

6. Which Toronto Maple Leafs Player won the Lady Byng Memorial Trophy on more than one occasion?

a) Joe Primeau
b) Gordie Drillon
c) Syl Apps
d) Sid Smith

7. Which defunct OHL team did Doug Gilmour play for before being drafted to the NHL

a) Brantford Alexanders
b) Cornwall Royals
c) Detroit Compuware Ambassadors
d) Guelph Platers

Interesting Goaltending Trivial Factoids

• Curtis Joseph, one of the Leafs best goalies was undrafted into the NHL.
• David Ayres, a Toronto Marlies Zamboni driver was an emergency replacement for a game in Toronto. He played for parts of two periods but not for the Maple Leafs. Instead, he helped the Carolina Hurricanes embarrass the Buds
• The Leafs were also embarrassed when their goaltender Vesa Toskala let in one of the longest goals in NHL history. The puck traveled 197 feet before bouncing five times to beat Toskala.
• Jacques Plante owns the Maple Leafs best save percentage at 0.925. He had three years in Toronto.
• Felix Potvin was Andrew Raycroft’s backup goalie with the Bruins in 2003-04. In 2006-07, Raycroft happened to be the man to beat Potvin’s record for consecutive games played by a Maple Leafs goalie.

Hard Level Answers

1. Who was the youngest player to captain the Toronto Maple Leafs?

A: d) Rick Vaive
Rick Vaive was 22 when he was named captain for the 1981-82 season. Others were also young when they got a ‘C’ placed on their jerseys. Hap Day was 26 when he got the honour. Syl Apps was also 26 years old. Ted Kennedy was the second youngest at 23 years old when he was given the captaincy for the 1948-49 season. Dion Phaneuf was 25 and current Leafs captain, John Tavares, was 29.

2. Which legendary player scored their last Stanley Cup Playoffs goal against the Toronto Maple Leafs?

A: c) Maurice Richard
Passed to him by his brother Henri, Rocket Richard scored his last goal in his final NHL game. It was a contest that ended with the Canadiens lifting the Stanley Cup. That 1960 cup was their fifth consecutive championship.

3. True or False: The Toronto Maple Leafs are the only Original Six team to finish the season in fourth place and win the Stanley Cup

A: a) True
The Leafs were 22-25-13 at the end of the 1948-49 season heading into the playoffs. They didn’t allow their position to thwart their chances at winning the cup. Toronto went on to beat the Boston Bruins in the Semi-Finals and swept the Detroit Red Wings in the Stanley Cup Finals.

4. Robert Reichel put the puck in his own net to give which Sabres goaltender an NHL goal?

A: d) Mika Noronen
There was a crazy game in 2004 when the Maple Leafs had a hot start. They came out to a 3-0 lead, chasing Martin Biron from his net. This gave Mika Noronen the chance to help his team. That’s exactly what he did. The Buffalo Sabres came back to not just tie the game but take the lead 5-4.

The Leafs pulled their goalie in favour of an extra attacker. This hurt them when Robert Reichel made an unadvised pass. He tried to center a pass from behind Noroven’s net, but instead of finding a teammate, the puck missed every stick and sailed down the ice and into Toronto’s goal. Since Noronen was the last Sabre to touch the puck, he was credited with the goal.

5. Who is the only Toronto Maple Leafs Player to wear #99 on his sweater?

A: b) Wilf Paiement 
The most famous person to ever wear the number 99 was the Great One, Wayne Gretzky. The only person to wear it with the Leafs was Wilf Paiement. He did so in his three seasons with the team, from 1979-1982.

6. Which Toronto Maple Leafs Player won the Lady Byng Memorial Trophy on more than one occasion?

A: d) Sid Smith
All the players listed won the Lady Byng at one point in their respective careers, however, only Sid Smith won it twice. Alexander Mogilny also won the award while with the Maple Leafs. He too captured the prize just once.

7. Which defunct OHL team did Doug Gilmour play for before being drafted to the NHL?

A: b) Cornwall Royals
Doug Gilmour played in three junior leagues. He played for the Kingston Voyageurs in the Metro Jr. B Hockey League (MJBHL) and the Belleville Bulls in the Ontario Junior A Hockey League (OPJHL) that same year. He then joined the Cornwall Royals in Quebec Major Junior Hockey League and stayed with the team when it moved to the Ontario Hockey League (OHL).

Gilmour was drafted by the St Louis Blues in the seventh round of the 1982 NHL Entry Draft. He was the steal of the draft, going 134th overall.

Impossible Level Answers

1. How many hat tricks did Darryl Sittler have?

A: d) 18
Darryl Sittler actually leads the franchise with the most career hat tricks. He had 18.

2. Which former Toronto Maple Leafs coach owns the league record for leading his teams to the most Stanley Cup Finals?

A: b) Dick Irvin
Dick Irvin led his teams to a total of 16 Stanley Cup finals. He reached that total by combining his coaching record from the Chicago Blackhawks (1), Maple Leafs (7), and Montreal Canadiens (8). Irvin won one cup with the Leafs and three more with the Habs.

3. Who did the Toronto Maple Leafs Draft in the third round of the 2007 NHL Entry Draft?

A: b) Dale Mitchell
All the players listed were drafted in 2007. Two of them went in the third round. Yannick Weber went 73rd overall. One slot later, Toronto took Dale Mitchell. Though he looked like a promising prospect, once recording 43 goals and 37 assists in a season for the Oshawa Generals, Mitchell never played a single NHL game.

Carl Gunnarsson was the Leafs best pick in the draft. They got him in the seventh round and he spent five seasons playing for the team. Though he didn’t play as many games for the Leafs, Matt Frattin did manage to get into action over multiple seasons for the team. Toronto took him in the fourth round. They didn’t have a pick in either the first or second rounds.

4. How many goals did the franchise leader Mats Sundin score with the Maple Leafs?

A: c) 420
Sundin scored a total of 564 goals in his career. He had 420 of them with the Maple Leafs. He also had 135 in the four years he played for the Nordiques and finished his career adding nine goals in his only season with the Canucks.

5. Which Toronto Maple Leafs player led the league in single-season penalty minutes most often?

A: a) Red Horner
Tiger Williams is the NHL leader in penalty minutes. He accumulated 3971 in his career, 1670 in his six years with the Maple Leafs. He was the single-season pims leader thrice, twice with the Leafs and the third time as a Vancouver Canuck.

Second on the all-time list is Dale Hunter (3565) who never played with Toronto. He also never led the season in penalty minutes. Tie Domi did lead the league in this category once, in the 1993-94 season. Domi ranks third all-time with 3515 penalty minutes.

Gary Roberts is 19th all-time in total penalty minutes. He never led the league when he played. This was Red Horner‘s specialty. He was the leader in seven seasons. He also finished eight minutes behind Art Coulter, which would have given Horner eight straight campaigns as the league’s top offender.

6. The fastest goals in Maple Leafs history were scored just seven seconds into the game. Which two players recorded those goals?

A: a) Mitchell Marner and Charlie Conacher
Mitch Marner scored his seven-second marker on Jan. 3, 2019 against the Minnesota Wild. It was a game that the Leafs would go on to lose. Charlie Conacher potted his quick goal against the Bruins on Feb. 6, 1932. The Leafs blanked Boston that game 6-0 and Conacher scored again in the second period of that game.

7. Dave Andreychuk got married in 1991, a year before joining the Leafs. What’s his wife’s name?

a) Sue
Dave Andreychuk married his wife Sue while still playing with the Sabres. He and Sue have three daughters, Taylor, Caci and Brooke. They used to live in in East Amherst, New York but since Andreychuk took a job with the Tampa Bay Lightning’s front office the family relocated to Florida.

Do you know your Leafs trivia? Comment below on how you fared.