History of the Toronto Maple Leafs This is a history of the Toronto Maple Leafs of the National Hockey League . Early years ( 1917 – 28 ) . The beginnings of the Maple Leafs NHL franchise arose out of a long - running dispute between Eddie Livingstone , owner of the National Hockey Association ' s Toronto Blueshirts , and his fellow NHA owners . By the fall of 1917 , the owners of the NHA ' s other four clubs — the Montreal Canadiens , Montreal Wanderers , Ottawa Senators and Quebec Bulldogs were eager to disassociate themselves from Livingstone . They soon discovered that the NHA ' s constitution didn ' t allow them to simply vote Livingstone out . With this in mind , they met in Montreal on November 22 and created a new league — the National Hockey League . However , they didn ' t invite Livingstone to join them , effectively leaving him in a one - team league . On paper , they also remained members of the NHA and were able to vote down Livingstone ' s attempts to keep that league operating . Torontos / Arenas ( 1917 – 1919 ) . However , the other clubs and arena owners felt it would be unthinkable not to have a team from Toronto ( Canada ' s second - largest city at the time ) in the new league . Also , the new league needed a fourth team to balance the schedule because the Bulldogs had run into financial trouble and opted to suspend operations ( as it turned out , they wouldn ' t ice a team until 1920 ) . Accordingly , the new league granted a ' temporary ' franchise for Toronto to the Toronto Arena Company , owners of the Mutual Street Arena ( also known as the Arena Gardens ) , to use the Blueshirts ' players for the season until the dispute with Livingstone could be resolved . The Arena would handle the settlement with Livingstone out of the club revenues . Under manager Charlie Querrie and coach Dick Carroll , the Toronto team won the Stanley Cup in the NHL ' s inaugural season . The team actually did not have an official name during that season , but was still unofficially called " the Blueshirts " and " the Torontos " by the newspapers of the day , as well as by some fans . Although the roster was comprised mainly of former Blueshirts , the Maple Leafs do not claim the Blueshirts ' history as their own . In 1918 , the NHA voted once again against playing and the other owners made plans to operate the NHL for a second season . Since the Torontos had won the Cup , even more revenue was at stake and Livingstone held out for $ 20 , 000 , though the Arena offered $ 6 , 000 . This led to Livingstone filing another lawsuit , this against the Arena Company . In response , instead of returning the players to Livingstone , or even paying Livingstone , the Arena Company returned its temporary franchise to the NHL and immediately formed a new club , the Toronto Arena Hockey Club , popularly known as the Toronto Arenas , with auditor Hubert Vearncombe as team president . The new club was a self - contained corporation within the Arena Company ' s corporate structure , and could thus exist separate from any legal action . This new club immediately applied for membership in the NHL , and was duly admitted as a full member in good standing . ( The Maple Leafs themselves say they were known as the Arenas during their first season , but the name " Arenas " was not recorded to commemorate the team ' s 1918 Cup victory until 1947 . ) At the same time , the Arena Company board decided that only NHL teams would be allowed to play at the Arena Gardens , effectively foreclosing Livingstone ' s efforts to resurrect the NHA . Livingstone ' s suit dragged through the courts for nearly a decade . Although the courts ultimately decided in his favour , but never got his team back . Mounting legal bills from the dispute forced the Arenas to sell most of their stars , resulting in a horrendous five - win season in 1918 – 19 . With the club losing money and no hope of catching Ottawa and Montreal in the standings in a three - team league , they requested permission to suspend operations in late February 1919 . League president Frank Calder persuaded the team to play its 18th game on February 20 , after which the league ended the regular season and immediately proceeded to the playoffs . The Arenas ' . 278 winning percentage that season is still the worst in franchise history . However , since the 1919 Stanley Cup Finals ended without a winner , the Arenas proclaimed themselves world champions by default . Toronto St . Pats ( 1919 – 1927 ) . In 1919 , Livingstone won a $ 20 , 000 judgement against the Arena Company , which promptly declared bankruptcy to avoid paying . The Toronto NHL franchise was put up for sale and Querrie put together a group that mainly consisted of the people who had run the senior amateur St . Patricks team in the Ontario Hockey Association the previous year . The new owners renamed the team the Toronto St . Patricks ( or St . Pats for short ) . Among the officers of the St . Patrick ' s Professional Hockey Club Ltd . at the start of the 1919 – 20 season were president Fred Hambly , vice - president Paul Ciceri , secretary - treasurer Harvey Sproule , Charlie Querrie , and player - coach Frank Heffernan . The jersey colour was changed from blue to green . The 1921 – 22 NHL season led to the St . Pat ' s only Stanley Cup win . The team finished second to the Ottawa Senators , but caught fire in the playoffs . The St . Pats defeated the Senators in a two - game total goals series 5 – 4 . The team then traveled to Vancouver to take on the Millionaires , winning the series 3 – 2 and the Cup . ( see 1922 Stanley Cup Finals ) . The team was led by Babe Dye who scored 11 goals in the 7 playoff games , and John Ross Roach who had two shutouts . The next two seasons the St . Pats did not make the playoffs , but qualified second in 1924 – 25 , which had expanded the number of qualifiers to three as the Maroons and Bruins joined as expansion franchises . This meant a playoff with the Canadiens with the winner to play the Hamilton Tigers , the regular season champion . The St . Pats were defeated in what turned out to be the league finals as the Tigers were suspended . The next two seasons the St . Pats did not make the playoffs . During the mid - 1920s , the St . Pats allowed other teams to use the Mutual Street Arena in the early and late months of the season , when it was usually too warm for proper ice . The Arena was the only facility east of Manitoba with artificial ice . The Conn Smythe era . Querrie lost a lawsuit to Livingstone and decided to put the St . Pats up for sale . He gave serious consideration to a $ 200 , 000 bid from a Philadelphia group . However , Toronto Varsity Graduates coach Conn Smythe put together an ownership group of his own and made a $ 160 , 000 offer for the franchise . With the support of St . Pats shareholder J . P . Bickell , Smythe persuaded Querrie to reject the Philadelphia bid , arguing that civic pride was more important than money . After taking control on Valentine ' s Day 1927 Smythe immediately renamed the team the Maple Leafs . ( The Toronto Maple Leafs baseball team had won the International League championship a few months earlier and had been using that name for 30 years . ) There have been numerous reasons cited for Smythe ' s decision to rename the team . The Maple Leafs say that the name was chosen in honour of the Maple Leaf Regiment from World War I . Another story says that Smythe named the team after a team he ' d once scouted , called the East Toronto Maple Leafs . Smythe ' s name was initially kept in the background , even though he was the largest shareholder . When the newly renamed Toronto Maple Leaf Hockey Club Ltd . promoted a public share offering to raise capital , it only disclosed that " one of the most prominent hockey coaches in Toronto " would be taking over management of the club . That prominent coach turned out to be Smythe , who installed himself as general manager . Initial reports were that the team ' s colours would be changed to red and white , but the Leafs were wearing white sweaters with a green maple leaf for their first game on February 17 , 1927 . The next season , the Leafs appeared for the first time in the blue and white sweaters they have worn ever since . While the Leafs say that blue represents the Canadian skies and white represents snow , it is also true that top - level Toronto teams have worn blue since the Toronto Argonauts adopted blue as their primary colour in 1873 . Another theory is that Smythe changed the colours as a nod to his high school alma mater , Upper Canada College , whose teams have worn blue and white since 1829 and the University of Toronto whose teams have also worn blue and were called the Varsity Blues . After four more lacklustre seasons ( including three with Smythe as coach ) , Smythe and the Leafs debuted their new arena , Maple Leaf Gardens , with a 2 – 1 loss to the Chicago Blackhawks on November 12 , 1931 . Led by the " Kid Line " ( Busher Jackson , Joe Primeau and Charlie Conacher ) and coach Dick Irvin , the Leafs would capture their third Stanley Cup victory during the first season in their new digs . They would go the distance in 1932 , vanquishing Charlie Conacher ' s older brother Lionel Conacher and his Montreal Maroons in the first round , then in the semi - finals against the Boston Bruins , winning in the sixth overtime of the final game , and would not be overwhelmed in the Stanley Cup Finals by the hated New York Rangers . Smythe took particular pleasure in defeating the Rangers that year ; he had been tapped as the Rangers ' first general manager and coach in the Rangers ' inaugural season ( 1926 – 27 ) , but had been fired in a dispute with Madison Square Garden management . the next season , only to be upended by the Rangers . The Leafs ' star forward , Ace Bailey , was nearly killed in 1933 when Boston Bruins defenceman Eddie Shore checked him from behind into the boards at full speed . Maple Leafs defenceman Red Horner was able to knock Shore out with a punch , but it was too late for Bailey , who was by now writhing on the ice , had his career ended . Undeterred , the Leafs would reach the finals five more times in the next seven years , but would not win , bowing out to the now - defunct Maroons , the Detroit Red Wings in 1936 , the Chicago Black Hawks in 1938 , Boston in 1939 , and the hated Rangers in 1940 . After the 1940 loss , Smythe talked the then - moribund Canadiens into hiring Irvin as coach . Irvin was replaced in Toronto by former Leafs captain Hap Day . Toronto looked sure to suffer a similar fate in 1942 , down three games to none in a best - of - seven final in 1942 against Detroit . However , fourth - line forward Don Metz would galvanize the team , coming from nowhere to score a hat trick in game four and the game - winning goal in game five , with the Leafs winning both times . Captain Syl Apps had won the Lady Byng Memorial Trophy that season , not taking one penalty and finishing his ten - season career with an average of 5 minutes , 36 seconds in penalties a season . Goalie Turk Broda would shut out the Wings in game six , and Sweeney Schriner would score two goals in the third period to win the seventh game 3 – 1 and the stanley cup . No other team has repeated a comeback like this in a stanley cup final since . Apps told writer Trent Frayne in 1949 , " If you want me to be pinned down to my [ biggest night in hockey but also my ] biggest second , I ' d say it was the last tick of the clock that sounded the final bell . It ' s something I shall never forget at all . " It was the first time a major pro sports team came back from behind 3 – 0 to win a best - of - seven championship series . Three years later , with their heroes from 1942 dwindling ( due to either age , health , or the war ) , the Leafs turned to lesser - known players like rookie goalie Frank McCool and defenceman Babe Pratt . They would upset the Red Wings in the 1945 finals . In the 1946 - 47 NHL season , Maple Leaf Gardens was the first arena in the NHL to have Plexiglas inserted in the end zones of the rink . The powerful defending champion Montreal Canadiens and their " Punch Line " ( Maurice " Rocket " Richard , Toe Blake and Elmer Lach ) would be the Leafs ' nemesis two years later when the two teams clashed in the 1947 finals . Ted " Teeder " Kennedy would score the game - winning goal late in game six to win the Leafs their first of three straight Cups — the first time any NHL team had accomplished that feat . With their Cup victory in 1948 , the Leafs moved ahead of Montreal for the most Stanley Cups in franchise history . It would take the Canadiens 10 years to reclaim the record . The Leafs and Habs would meet once again in the finals in 1951 , with all five games going to overtime . Tod Sloan scored with 42 seconds left in the third period of game five to send it to an extra period , and defenceman Bill Barilko , who had scored only six goals in the regular season , scored the game - winner to win Toronto their fourth Cup in five years . Barilko ' s glory , however , was short - lived : he disappeared in a plane crash near Timmins , Ontario , barely four months after that historic moment . Barilko ' s legacy is still remembered over 50 years later , and The Tragically Hip ' s song " Fifty Mission Cap " is based on his plight . New owners , new dynasty in the 1960s . Toronto was unable to match up with their Cup - winning teams of the 1940s and 1951 for a long time , and stronger teams like Detroit and Montreal won the Cup year after year . In fact , the Habs ' 1950s dynasty closed with a last - round Maple Leaf sweep . They did not win another Stanley Cup until 1962 . Before the 1961 – 62 season , Smythe sold nearly all of his shares in Maple Leaf Gardens to a partnership of his son Stafford Smythe , newspaper baron John Bassett and Toronto Marlboros president Harold Ballard . The sale price was $ 2 . 3 million — a handsome return on his original investment 34 years earlier . According to Stafford ' s son Thomas , Conn Smythe said years later that he expected to sell his shares only to his son and would not have sold his shares to the partnership . However , it is not likely that Conn Smythe could have believed that Stafford could have raised the money needed to make the deal on his own . This purchase gave the three control of about 60 % ownership of the Leafs and Gardens . And then , Toronto was able to reel off another three straight Stanley Cup victories from 1962 to 1964 , with the help of Hall of Famers Frank Mahovlich , Red Kelly , Johnny Bower , Dave Keon , Andy Bathgate and Tim Horton , and under the leadership of coach and general manager Punch Imlach . However , Bathgate claimed after 1964 – 65 that all the autocratic Imlach said to himself and Mahovlich was insulting : " “ Imlach never spoke to Frank Mahovlich or myself for most of the season , and when he did , it was to criticize . Frank usually got the worst . We are athletes , not machines , and Frank is the type that needs some encouragement , a pat on the shoulder every so often . ” " It was Bathgate ' s one - way ticket to the floundering Red Wings , but Toronto would , for a few more years , keep " The Big M . " In 1967 , the Leafs and Canadiens met in the Cup finals for the last time . Montreal was considered to be a heavy favourite as analysts said that the Leafs were just a bunch of has - beens . But Bob Pulford scored the double - overtime winner in game three , Jim Pappin got the series winner in game six , and Keon won the Conn Smythe Trophy as most valuable player of the playoffs as the Maple Leafs won the Stanley Cup in six games . The Leafs have not won the Stanley Cup since . The next two seasons saw a great deal of turnover , engineered by Imlach , who detested the new Players ' Association headed by Maple Leaf players . Bobby Baun and Kent Douglas were left unprotected in the expansion draft . In 1968 , Mahovlich was traded to Detroit in a blockbuster trade . But there was no improvement in the team . After a disastrous first - round playoff loss to Boston in 1969 , Smythe fired Imlach . The Ballard years . Following Stafford Smythe ' s death , Harold Ballard bought Stafford Smythe ' s shares , taking control of the team as of February , 1972 , under terms of Stafford Smythe ' s will , allowing each partner to buy the other ' s shares upon their death . Stafford Smythe ' s brother Hugh also sold his shares to Ballard , ending the Smythe family ' s 45 - year involvement in the NHL . Stafford Smythe ' s son Thomas alleges that Ballard wrote the will to his advantage . One of the most detested owners in NHL history , he traded away many of the team ' s most popular players . He also blocked Keon from signing with another NHL team when his contract ran out in 1975 , forcing him to jump to the Minnesota Fighting Saints of the World Hockey Association . Ballard assumed ( correctly ) that the Leafs would continue to sell out regardless of the team ' s on - ice quality , and refused to raise the payroll any higher than necessary to be profitable . During the 1970s , with the overall level of talent in the league diluted by the addition of 12 new franchises and the rival WHA , the Leafs , led by a group of stars such as Darryl Sittler , Lanny McDonald , enforcer Tiger Williams , Ian Turnbull and Borje Salming were able to ice competitive teams for several seasons . On February 7 , 1976 , Sittler would score six goals and four assists against the Bruins to establish an NHL single - game record that still stands more than 30 years later . On February 2 , 1977 , Toronto Maple Leafs defenceman Ian Turnbull would be the first player in NHL history to score five goals on five shots . Despite the performances , the Leafs were not able to qualify for the Stanley Cup Finals . They only once made it past the second round of the playoffs , besting the New York Islanders , a soon - to - be dynasty , in the 1978 quarter - finals , only to be swept by their arch - rivals the Montreal Canadiens , in the semi - finals . In July 1979 , Ballard brought Imlach , a longtime friend , back to the organization as GM . When the Leafs traded McDonald , a close friend of Sittler , to the moribund Colorado Rockies on December 29 , 1979 ; a member of the Leafs anonymously told the " Toronto Star " that Ballard and Imlach would " do anything to get at Sittler " and traded McDonald to undermine Sittler ' s influence on the team . Sittler , along with other Leafs who were members of the NHL Players Association , was agitating for a better contract . Angry teammates trashed their dressing room in response , and Sittler temporarily resigned his captaincy . NHL executive director Alan Eagleson , who was also Sittler ' s agent , called the trade " a classless act . " Sittler himself was gone two years later , when the Leafs traded him to the Philadelphia Flyers . He left as the franchise ' s all - time leading scorer . The McDonald trade sent the Leafs into a downward spiral . They finished five games under . 500 and only made the playoffs due to the presence of the Quebec Nordiques , a refugee from the WHA , in the Adams Division . Ironically , Ballard had opposed taking the Nordiques and three other WHA teams into the NHL for the start of the 1979 – 80 season . He had never forgiven the WHA for nearly decimating his roster in the early 1970s , and the addition of three Canadian teams ( the Nordiques , Winnipeg Jets and Edmonton Oilers ) significantly reduced the Leafs ' revenue from " Hockey Night in Canada " broadcasts ( which was now split six ways rather than three ) . For the next 12 years , the Leafs were barely competitive , not posting another winning record until 1992 – 93 . They missed the playoffs six times and only finished above fourth in their division once ( in 1990 , the only season where they even posted a . 500 record ) . They only made it beyond the first round of the playoffs twice ( in 1986 and 1987 , advancing to the division finals ) . The low point came in 1984 – 85 , when they finished 32 games under . 500 , the second - worst record in franchise history ( their . 300 winning percentage was only 22 percentage points higher than the 1918 – 19 Arenas ) . Many times , they made the playoffs with horrendous records . In 1987 – 88 , for instance , they finished with the second - worst record in the league ( and the third - worst record in franchise history , at . 325 ) , and only one point ahead of the Minnesota North Stars for the worst record . However , the Norris Division was so weak that year ( only the Red Wings finished with a winning record ) that the Leafs still made the playoffs . They gave the Red Wings a surprisingly tough series in the first round , pushing them to six games . Many Leafs fans consider Ballard ' s tenure as owner to be the darkest era in team history ; indeed , they only notched six winning seasons during Ballard ' s 18 - plus years as majority ow , never finished above third in their division and only got out of the second round twice . The Leafs ' poor record resulted in several high draft picks . Wendel Clark , the first overall pick in the 1985 draft , was the lone success from the entry drafts of this period and went on to captain the team . Resurgence in and after the 1990s . Ballard died in 1990 . A year later , supermarket tycoon Steve Stavro , a longtime friend of Ballard ' s , bought the team from Ballard ' s estate in partnership with the Ontario Teachers ' Pension Plan . Unlike Ballard , Stavro hated the limelight and rarely interfered in the Leafs ' hockey operations . After 1991 – 92 , ex - Calgary Flames GM Cliff Fletcher took over the team . He made a series of trades and free agent acquisitions which turned the Leafs from an also - ran to a contender almost overnight . Unlike the league ' s other Canadian teams , the Leafs were not seriously impacted by the escalation of player salaries in the early 1990s . In fact , they actually thrived , as they were based in the league ' s fourth largest market . The new stars paid almost immediate dividends in 1992 – 93 . Doug Gilmour , who had come over from the Flames the previous season , scored 32 goals and 95 assists to lead the team in scoring . Dave Andreychuk had come to the Leafs from the Buffalo Sabres and would score 25 goals in his first 31 games as a Leaf as well as being the league ' s leading power - play goal scorer . Netminder Felix Potvin was also solid with an NHL - best 2 . 50 goals - against average . Toronto finished with a franchise - record 99 points , good enough for third place in the Norris Division and the eighth - best record in the league . The Leafs dispatched the Detroit Red Wings in the first round with an overtime winner from Nikolai Borschevsky in game seven , then won the Norris Division final by defeating the St . Louis Blues , also in seven games . With Montreal facing the New York Islanders in the Wales Conference final , Canadians and hockey purists began dreaming of a Montreal - Toronto Cup final , as the Leafs faced the Los Angeles Kings , led by their captain Wayne Gretzky , in the Campbell Conference final . The Leafs were up 3 – 2 in the series , but lost game six . Gretzky ' s hat trick in game seven would finish the Leafs ' run , and it would be the Kings who would move on to the Finals against the Canadiens . The Leafs had another strong season in 1993 – 94 , finishing with 98 points . This was good enough for the fifth - best record in the league — their highest overall finish in 16 years . However , despite finishing one point above the Calgary Flames , the Leafs were seeded third in the Western Conference ( formerly the Campbell Conference ) by virtue of the Flames ' Pacific Division title . However , a six - game series against the Blackhawks and a seven - game series against the San Jose Sharks took their toll on the team ; they were defeated by the Vancouver Canucks - - a team that finished 13 points below them in the regular season — in five games . After two years out of the playoffs in the late 1990s , the Leafs made another charge during the 1999 playoffs after moving from Maple Leaf Gardens to the new Air Canada Centre . Mats Sundin , who had joined the team from the Quebec Nordiques in a 1994 trade involving Wendel Clark , had one of his most productive seasons , scoring 31 goals and totaling 83 points . Sergei Berezin scored 37 goals , Curtis Joseph won 35 games with a 2 . 56 GAA , and enforcer Tie Domi racked up 198 penalty minutes . The Leafs eliminated the Philadelphia Flyers and Pittsburgh Penguins in the first two rounds of the playoffs , but lost in five games to the Buffalo Sabres in the Eastern Conference Finals . The Maple Leafs would reach the second round in both 2000 and 2001 , losing both times to the New Jersey Devils , who would make the Stanley Cup Finals both seasons . The 2000 season was particularly notable because it marked the Leafs ' first division title in 37 years , as well as the franchise ' s first - ever 100 - point season . The season ended on a particular low , however , with the Leafs being held to just 6 shots in the final contest ( game six ) against the Devils . In 2002 , they would dispatch the Islanders and their trans - Ontario rivals , the Ottawa Senators , in the first two rounds , only to lose to the Cinderella - story Carolina Hurricanes in the Conference Finals . The 2002 season was particularly impressive in that the Leafs had many of their better players sidelined by injuries , but managed to make it to the conference finals due to the efforts of lesser - known players who were led mainly by Gary Roberts , who put up a heroic fight , although they would eventually fall to the Hurricanes . Joseph left to go to the defending champion Red Wings in the 2002 off - season ; the team almost immediately found a replacement in veteran Ed Belfour , who came over from the Dallas Stars and had been a crucial part of their 1999 Stanley Cup run . Belfour could not help their playoff woes in the 2003 playoffs , however , as they lost to Philadelphia in seven games in the first round . The 2003 – 04 season started in an uncommon way for the team , as they held their training camp in Sweden , and playing in the NHL Challenge against teams from Sweden and Finland . That year , the Leafs posted a franchise - record 103 points . They also finished with the fourth - best record in the league — their best overall finish in 41 years . They also managed a . 628 win percentage , their best in 43 years ( and the third - best in franchise history ) . They defeated the Senators in the first round of the playoffs for the fourth time in five years , but lost to the Flyers in the second round in six games . The Leafs did not make the playoffs in 2006 , finishing tenth in the Eastern Conference . During the 2007 - 2008 season again the Leafs struggled in their division , only this time , their Captain , Mats Sundin was asked to waive his no - trade claus to try and advance the team ' s hopes of the playoffs , and a more promising 2008 - 2009 season . Sundin declined , acknowledging that from his perspective the Leafs still had the chance to make the playoffs , and that he did not want to be a " rental player " to a playoff bound team . The other glaring factor , though rarely discussed was the obvious contractual obligation both parties had entered into when Sundin ' s contract was originally written - the no trade claus . It is widely speculated that culmination of these events soured Leaf fans and also strained relations between Sundin and the Toronto organization . Ultimately , Toronto did not make the playoffs during the 2007 - 2008 season , and Mats Sundin was an unrestricted free agent , contemplating retirement from the NHL . Following approximately 9 months of contemplation , Mats Sundin returned to the NHL signing with the Vancouver Canucks . Mats cited his decision to return to the NHL was based partly on " having a chance at winning the Stanley Cup " . Toronto faced Vancouver two times during the 2008 - 2009 season , losing in both showdowns , most notably during a shoot out decision on February 21 , 2009 where Mats Sundin was honored at the ACC . He also scored the winning goal to defeat Toronto . The Toronto Maple Leafs are the only Original Six franchise to have neither won the Stanley Cup , or a Conference title , since the 1967 NHL Expansion .