List of Stanley Cup challenge games This is a list of Stanley Cup challenge games from 1894 to 1914 . During this period , the Stanley Cup was a " challenge trophy " ; the champions held onto the Cup until they either lost their league title to another club , or a champion from another league issued a formal challenge and subsequently defeated the reigning Cup champion in a special game or series . The playoff format for each challenge varied depending on what the two competing clubs agreed to . Before 1912 , challenges could take place at any time , given the appropriate rink conditions , and it was common for teams to defend the Cup numerous times during the year . In 1912 , the Cup ' s trustees declared that the Cup was only to be defended at the end of the champion team ' s regular season . Also during this era , all of the leagues that played for the trophy had no annual formal playoff system to decide their own respective championships ; whoever finished in first place after the regular season won the league title . Thus , a few league championship games or series were held just to break first place ties and determine who would keep the Cup . These league title games have historically been listed along with the regular inter - league Cup challenges . Season - by - Season Summary . This table lists all the champions of the Stanley Cup per hockey season , ( which does not have official dates as rinks were natural ice , so the season roughly corresponds to winter ) for the ' challenge era . ' The leagues typically started close to the beginning of the calendar year and ended in early March . 1893 – 94 . The first Stanley Cup playoff game occurred on March 17 , 1894 . At the end of the Amateur Hockey Association of Canada season , four teams tied for the AHAC championship with records of 5 – 3 – 0 . This created problems for the AHAC governors and the Cup ' s trustees since there was no tiebreaking system in place . After long negotiation and the withdrawal of Quebec from the championship situation , it was decided that a three - team tournament would take place in Montreal , with the Ottawa Hockey Club getting a bye to the finals ( being the sole " road " team ) . In the first Stanley Cup playoff game ever , the Montreal Hockey Club defeated the Montreal Victorias , 3 – 2 . Five days later in the first Stanley Cup Final game , the Montreal HC successfully defended their title with a 3 – 1 win over Ottawa . Later in the year , the Cup trustees accepted a challenge from the squad from Osgoode Hall , the champions of the Ontario Hockey Association ( OHA ) . However , the series was eventually cancelled because of the lack of ice . 1894 – 95 . On March , 8 , 1895 , the Montreal Victorias won the 1895 AHAC title and thus the Stanley Cup , after finishing the season with a 6 – 2 record . However , a challenge game was scheduled earlier for the next day between the previous year ' s champion Montreal HC and the squad from Queen ' s University , which was then part of the OHA . Thus , it was decided that if the Montreal HC won the challenge match , the Victorias would become the Stanley Cup champions . The Montreal HC would eventually win the game , 5 – 1 , and their crosstown rivals were crowned the champions . Billy Barlow , the star player of Montreal was not able to play and Clarence McKerrow took his place . McKerrow had not played any games for Montreal , and could be considered a ringer , but there was no protest from Queen ' s . The Queen ' s team , although described as looking fast in their tiger jerseys , were no match for Montreal and the game proved uninteresting . 1895 – 96 . The first successful challenge to the Cup came in February 1896 by the Winnipeg Victorias , the champions of the Manitoba Hockey Association ( MHA ) . On February 14 , Winnipeg beat defending champion Montreal , 2 – 0 , becoming the first team outside the AHAC to win the Cup . 1896 – 97 . The Montreal Victorias won the 1896 AHAC title by finishing the season with a 7 – 1 record , and subsequently demanded a rematch for the Cup . However , it was delayed until December 30 due to unsuitable ice conditions in Montreal . In what was said to be the most anticipated hockey game of the time , the Montreal Victorias defeated the Winnipeg Victorias , 6 – 5 , to reclaim the Cup . 1897 – 98 . Another 7 – 1 record earned the Montreal Victorias the 1897 AHAC title , and the team subsequently received a challenge from the Ottawa Capitals , champions of the Central Canada Hockey Association ( CCHA ) . It was originally scheduled as the first best - of - three challenge , but the series ended after the first game because the Victorias clearly was the superior team with a 15 – 2 victory . The Montreal Victorias again won the AHAC championship after finishing the 1898 AHAC season undefeated with an 8 – 0 record . As a result , no one challenged the Victorias for the Cup . 1898 – 99 . Prior to the start of the 1898 – 99 season , the AHAC dissolved . The defending Cup champion Montreal Victorias along with several other former AHAC members formed the Canadian Amateur Hockey League ( CAHL ) . Montreal then received another challenge from the MHA ' s Winnipeg Victorias . This time , it was decided that they would play a two - game total goals series in February 1899 . The second game ended in controversy . With Montreal leading the game 3 – 2 with about 12 minutes left in the game , Montreal ' s Bob Macdougall violently slashed Winnipeg ' s Tony Gingras . As Gingras was carried off the ice , referee Bill Findlay only called Macdougall for a two minute minor . Angry that he should have been accessed a larger penalty , Winnipeg went into their dressing room in protest . Insulted , Findlay abruptly went home , but returned after officials followed him on a sleigh and persuaded him to return . Once back at the rink , the referee gave Winnipeg 15 minutes to return to the ice themselves . They refused and thus Findlay disqualified the team and declared Montreal the winners . Two weeks after the Montreal Victorias defeated Winnipeg in their two - game total goals series , they lost the 1899 CAHL title , and thus the Cup , to the Montreal Shamrocks . The Shamrocks compiled a 7 – 1 season record while the Victorias finished one game back at 6 – 2 . The Shamrocks then played a challenge game against Queen ' s University on March 14 , defeating them 6 – 2 . 1899 – 1900 . The MHA ' s Winnipeg Victorias issued another challenge for the Cup . This time , a best - of - three series was played against the defending champion Montreal Shamrocks . Winnipeg won the first game , 4 – 3 , but Montreal prevailed in the next two games , 3 – 2 and 5 – 4 . In March , the Shamrocks finished the 1900 CAHL season in first place , and thus the league championship , with a 7 – 1 record and then received another challenge for the Cup . However , the Halifax Crescents of the Maritime Hockey League ( MaHL ) did not pose much of a threat as Montreal crushed them , 10 – 2 and 11 – 0 . 1900 – 01 . In January 1901 , the Winnipeg Victorias again challenged the Montreal Shamrocks for the Cup . This time , Winnipeg prevailed , sweeping the best - of - three series with scores of 4 – 3 and 2 – 1 . Game 2 was the first overtime game in Cup history with Dan Bain scoring at the four minute mark of the extra period . 1901 – 02 . In January 1902 , the OHA ' s Toronto Wellingtons challenged the Winnipeg Victorias for the Cup in a best - of - three series , but Winnipeg swept Toronto in two games with identical 5 – 3 scores . After the Montreal HC won the 1902 CAHL title in March , they promptly sent a challenge to the Winnipeg Victorias . In Game 1 of the best - of - three series , Winnipeg shutout Montreal , 1 – 0 . However , Montreal shutout Winnipeg in Game 2 , 5 – 0 , and then held on to a 2 – 1 victory in Game 3 . With the victory , the Montreal club won the Cup for the first time since 1894 . 1902 – 03 . Another Montreal HC vs . Winnipeg Victorias best - of - three challenge series was held in early 1903 . In the first game , defending champion Montreal defeated Winnipeg , 8 – 1 . The second game was the first Stanley Cup challenge match to be replayed . Both teams skated to a 2 – 2 tie before the game had to be suspended at 27 : 00 of overtime because of a midnight curfew . It was then decided to discard the result and replay the game two days later . In the rescheduled contest , the Victorias won , 4 – 2 , to even the series . However , Montreal won the decisive third game , 4 – 1 , to retain the Cup . In March , the 1903 CAHL season ended with the Montreal Victorias and the Ottawa Hockey Club tied for first place with identical 6 – 2 records . To determine the CAHL champion , and thus succeed the Montreal HC as the Cup champion , a two - game total goals series was held between the two teams . The first game was held in Montreal ending in a 1 – 1 tie . The second game was played in Ottawa , with the Ottawas dominating the Victorias , 8 – 0 . The Ottawas thus won the Cup by winning the CAHL . As the new CAHL and Cup champions , the Ottawas accepted a challenge from the Rat Portage Thistles of the Manitoba & Northwestern Hockey Association ( MNWHA ) . Entering the best - of - three challenge series , the Thistles were younger and quicker than Ottawa ; only one player on the Thistles was over the age of 20 . However , poor soft ice conditions in Ottawa played a major factor as the Ottawas swept the series with scores of 6 – 2 and 4 – 2 . For their win , the Ottawa players each received a silver nugget from team director Bob Shillington . This is the origing of the nickname of the " Silver Seven . " 1903 – 04 . In January 1904 , a best - of - three Cup challenge series was held between the defending champion Ottawa Hockey Club ( aka " Silver Seven " ) and the MHA ' s Winnipeg Rowing Club . Ottawa crushed Winnipeg , 9 – 1 , in Game 1 but the Rowing Club rebounded with a 6 – 2 victory in the second game . The Silver Seven then won the deciding third game , 2 – 0 . This series marked the first time that goal lines were drawn across the ice from post to post . On January 30 , 1904 , a CAHL league game between the Ottawas and the Montreal Victorias started late and the game ended at the midnight curfew , with Ottawa leading 4 – 1 . The CAHL ordered the game to be replayed , and the ensuing debate caused the Ottawas to withdraw from the CAHL . The CAHL hoped that without Ottawa , the Cup would remain with the CAHL and be given to its new league champion , the Quebec Bulldogs . However , the Cup trustees thought otherwise , and although the Silver Seven were not affiliated with any league for the rest of the season , they could still receive challenges . About a month later , Ottawa swept a best - of - three Cup series against the OHA ' s Toronto Marlboros with scores of 6 – 3 and 11 – 2 . In early March , the Montreal Wanderers of the Federal Amateur Hockey League ( FAHL ) challenged the Senators for the Cup . But in Game 1 at Montreal , the match was tied , 5 – 5 , at the end of regulation and the Wanderers refused to play overtime with the current referee . The Cup trustees ordered the series to restart with both games played in Ottawa . However , Montreal refused unless the first game was replayed at home . As a result , the Wanderers were disqualified and thus the Silver Seven was automatically awarded the Cup . A week later , Ottawa HC was challenged by the MNHA ' s Brandon Wheat Cities , but prevailed in another two game sweep with scores of 6 – 3 and 9 – 3 . 1904 – 05 . The Ottawa HC joined the FAHL for the 1904 – 1905 season . Ottawa vs . Dawson City . In January 1905 , the Ottawas were challenged by the Dawson City Nuggets who travelled 4 , 000 miles ( 6 , 400 km ) from the Yukon to Ottawa for a best - of - three Cup challenge series . The Nuggets actually left Dawson City on December 19 , 1904 and travelled on a month - long journey by dog sled and walking ( Dawson to Whitehorse ) , ship ( Skagway to Vancouver ) , and train ( Whitehorse to Skagway , and Vancouver to Ottawa ) . Largely because of the long trip , they were no match for the Silver Seven . Ottawa defeated Dawson City in the first game by a score of 9 – 2 . Numerous Stanley Cup records were then set in the second game , including Frank McGee ' s 14 goals , and a 23 – 2 rout , the largest margin of victory for any challenge game or Stanley Cup Final game to date as of 2008 . Ottawa vs . Rat Portage . Ottawa eventually won the 1905 FAHL title by finishing in first place with a 7 – 1 record . Then in March , the Rat Portage Thistles issued another challenge to the Ottawas . Although the Thistles crushed Ottawa in the first game , 9 – 3 , Ottawa was without Frank McGee who did not play . However , McGee returned to lead the Ottawas to 4 – 2 and 5 – 4 victories in the second and third games to win the series . On the same day that the third game of the Thistles - Ottawa series was played , the 1905 CAHL season ended with the Montreal Victorias winning the title . The Cup trustees accepted their challenge , however , the Montreal - Ottawa series was eventually cancelled because the trustees and the Victorias could not agree on either the game dates or the playoff series format . 1905 – 06 . For the 1905 – 06 season , the Ottawa HC ( aka " Silver Seven " ) joined the new Eastern Canada Amateur Hockey Association ( ECAHA ) . In February , Ottawa played a best - of - three challenge series against OHA champion Queen ' s University , but the Senators proved to be the better team as they swept the series with 16 – 7 and 12 – 7 victories . About a week later , Smiths Falls , the FAHL champions , issued a challenge for the Cup , but they suffered the same fate as Queen ' s University . The Ottawas defeated them with scores of 6 – 5 and 8 – 2 to defend the Cup . Interestingly , Ottawa management was so impressed with Smiths Falls goalie Percy LeSueur that they signed him to join the Ottawas a few days after the series ended . The 1906 ECAHA season ended a few days later after the Smiths Falls - Ottawa series , with both Ottawa and the Montreal Wanderers tied for first place with identical 9 – 1 records . It was decided to hold a two - game total goals series to determine the league champion , and thus who would keep the Cup . The first game was played in Montreal where the Wanderers promptly crushed the Ottawas , 9 – 1 . Needing at least an eight - goal victory in the rematch in Ottawa , the newly signed LeSueur was named Ottawa ' s starting goalie , and the Ottawas jumped to a 9 – 1 lead to tie the series . But with under 5 minutes to go , Montreal ' s Lester Patrick scored twice to clinch the series for the Wanderers , winning the total - goals series , 12 – 10 and taking over the Stanley Cup . 1906 – 07 . In December 1906 , the New Glasgow Cubs , an amateur team from New Glasgow , Nova Scotia , issued a challenge to the Montreal Wanderers . In a two - game total goals series , Montreal easily defeated New Glasgow in both matches , 10 – 3 and 7 – 2 . This was the first series in which professional players played for the Stanley Cup , as the Wanderers and other teams in the ECAHA were starting to mix amateurs with pros in their squads . The Kenora Thistles ( formerly the Rat Portage Thistles before the city changed its name to Kenora in 1904 ) challenged the Montreal Wanderers for the Cup in January 1907 . Aided by future Hockey Hall of Fame rs Tom Hooper , Tommy Phillips , and Art Ross , the Thistles came away with 4 – 2 and 8 – 6 victories for a combined score of 12 – 8 to win a two - game total goals series . A " ringer " , Ross was a member of the Brandon Wheat Kings and was borrowed by Kenora for just the challenge games . In March , Kenora would play and win the Manitoba Professional Hockey League ( MPHL ) playoffs against Brandon to successfully defend the Cup . In a best - of - three , Kenora won 2 – 0 . In March , the Wanderers won the 1907 ECAHA title by finishing the season undefeated with a 10 – 0 record . Montreal then requested a rematch with Kenora for the Cup . However , there were disagreements between both teams . The Wanderers did not want the Thistles to use their " ringers " , Harry Westwick and Alf Smith from the Ottawa Senators . Kenora responded by refusing to play , citing the fact that Montreal used " ringers " in the earlier series . Eventually , the Wanderers withdrew their protest after the Thistles agreed to play the two - game total goals series in Winnipeg ; Winnipeg Arena was much larger and thus guaranteed more ticket sales for the clubs to share . In the end , Montreal overcame Westwick and Smith as they compiled a combined score of 12 – 8 to win the series . Most of the Wanderers ' margin - of - victory came in Game 1 as they defeated the Thistles , 7 – 2 . Kenora won Game 2 , 6 – 5 , but the one - goal victory was not enough . 1907 – 08 . Although the Montreal Wanderers won the 1908 ECAHA title by finishing the season with an 8 – 2 record , they played in three Cup challenges that season . In January , they defeated the 1907 FAHL champion Ottawa Victorias , 22 – 4 , in a two - game total goals series . Ernie Russell scored 10 goals as he led the Wanderers to 9 – 3 and 13 – 1 victories . The Winnipeg Maple Leafs of the MHL challenged Montreal for the Cup in March , but the Wanderers came away with 11 – 5 and 9 – 3 wins to clinch the two - game total goals series , 20 – 8 . Montreal ' s greatest challenge happened two days later when they played a single - elimination game against the Toronto Trolley Leaguers . Toronto was the champion of the newly established Ontario Professional Hockey League ( OPHL ) , and was the first all - professional team to compete for the Cup . However , the Wanderers prevailed , 6 – 4 , with two late goals by Ernie Johnson and Bruce Stuart . 1908 – 09 . In December 1908 , Montreal played its first Cup challenge of the season , this time against the Edmonton Hockey Club of the Alberta Amateur Hockey Association ( AAHA ) . Edmonton entered the series with an all - time high of six " ringers " . In Game 1 , Harry Smith scored 5 goals as he led the Wanderers to a 7 – 3 victory . The Edmontons won Game 2 , 7 – 6 , but Montreal took the two - game total goals series , 13 – 10 . Prior to the start of the new season , the Montreal HC and the Montreal Victorias , the last remaining amateur teams , left the ECAHA , and the league dropped " Amateur " from its name to become an all - pro league . The 1909 ECHA season ended with the defending Cup champion Montreal Wanderers finishing in second place with a 9 – 3 record , behind the first place Ottawa HC who finished at 10 – 2 . Thus Ottawa HC won the league championship and were awarded the Cup . Ottawa received a challenge only from the Winnipeg Shamrocks , but it was too late in the season to set a date . 1909 – 10 . In an effort to freeze out the Montreal Wanderers , the ECHA disbanded in December 1909 and a new league called the Canadian Hockey Association ( CHA ) was formed , deliberately designed to exclude the Wanderers . While the Wanderers were forced to join the newly formed National Hockey Association ( NHA ) , the defending Cup champion Ottawa HC still had to accept challenges . In January 1910 , they played a two - game total goals series against Galt , champions of the OPHL , but prevailed with 12 – 3 and 3 – 1 victories . Marty Walsh led Ottawa with 6 goals . Soon after the Galt - Ottawa challenge series ended , the CHA folded because of financial difficulties , and Ottawa was admitted into the NHA . The Senators then played a two - game total goals series against the Edmonton Eskimos , but Gordie Roberts ' 7 goals helped Ottawa to victories of 8 – 4 and 13 – 7 . When the 1910 NHA season ended in March , the Ottawas had to give the Cup to the Wanderers . Montreal finished in first place with an 11 – 1 record while Ottawa finished in second place at 9 – 3 . The Wanderers then accepted challenge from the Berlin Dutchmen , who succeeded Galt as the OPHL champions . In the single - elimination game , Ernie Russell scored 4 goals as he led Montreal to a 7 – 3 win . 1910 – 11 . The Ottawa HC captured the NHA championship , and thus the Cup , after finishing the 1910 – 11 season in first place with a 13 – 3 record . The Ottawas then played in two Cup challenges during the month of March . In a one game challenge on March 13 , Ottawa defeated Galt , 7 – 4 , aided by three goals by future hall of fame forward Marty Walsh . Three days later , the Ottawas played the Port Arthur Bearcats of the Northern Ontario Hockey League ( NOHL ) in another one - game final . Walsh scored ten goals as Ottawa crushed Port Arthur , 14 – 4 . 1911 – 12 . In 1912 , Cup trustees declared that the Cup was only to be defended at the end of the champion team ' s regular season . As a result , anyone who wanted to challenge for the Cup had to wait until the 1911 – 12 NHA season concluded . When it ended , the Ottawa HC finished in second place , with a 9 – 9 record , behind the Quebec Bulldogs , who posted a 10 – 8 record to take the league championship and take over the Cup . The Bulldogs then went on to sweep the Moncton Victorias of the Maritime Professional Hockey League ( MPHL ) in a best - of - three Cup challenge series , with 9 – 3 and 8 – 0 victories . 1912 – 13 . The 1912 – 13 NHA season ended with Quebec Bulldogs repeating as league champions . The Bulldogs then played a two - game total goals Cup challenge series versus the Sydney Millionaires of the MPHL , with Quebec winning 20 goals to 5 . Joe Malone scored 9 goals as he led the Bulldogs to a 14 – 3 win in the first game . Quebec then won the second by a score of 6 – 2 , with Joe Hall earning a hat trick . Later in the month , the Victoria Aristocrats of the Pacific Coast Hockey Association ( PCHA ) challenged Quebec . However , the Bulldogs refused to put the Cup on the line , so the two teams played a best - of - three exhibition series instead . In the first series ever between the champions of the two leagues , all of the games were played in Victoria , while the differing rules of the NHA and PCHA alternated between each contest . A major rule difference was the PCHA had seven - man rules while the NHA had six . The first game was played under PCHA rules and the Aristocrats recorded a 7 – 5 victory . Under NHA rules in the second game , Quebec won 6 – 3 . But in the third game , playing one half of the game using NHA rules , and the other PCHA rules , Victoria won the series with a decisive 6 – 1 victory . Many newspapers across the country declared Victoria as winners of the first " World Series of Hockey " . 1913 – 14 . At the end of the 1913 – 14 NHA season , the Toronto Blueshirts and the Montreal Canadiens were tied for first place with identical 13 – 7 records . To determine the NHA title and the new Cup champions , both teams played a two - game total goals series . Each team recorded shutouts on its home ice : Montreal won the first game , 2 – 0 , but Toronto came back to win the second game , 6 – 0 . The Blueshirts won the series , 6 goals to 2 . Game two in Toronto was the first Stanley Cup playoff game ever played on artificial ice . Later in the month , Toronto and the PCHA ' s Victoria Aristocrats played a best - of - five series for the Cup . However , Victoria neglected to file the formal proper challenge with the Cup trustees . Because of this , the trustees did not view the series as legitimate . As it turned out , the Blueshirts swept the series to successfully defend the Cup with scores of 5 – 2 , 6 – 5 in overtime , and 2 – 1 . The controversy would later set up an agreement between the NHA , the PCHA , and the Cup trustees in which the two leagues ' respective champions would face each other for the Cup . Table of participating teams . " Legend : SC = successful Stanley Cup challenge or defense of championship ( win ) ; UC = unsuccessful Stanley Cup challenge or defense of championship ( loss ) " The following 20 teams unsuccessfully challenged for a Stanley Cup only once : Berlin Dutchmen , Brandon Wheat Cities , Dawson City Nuggets , Edmonton Eskimos , Edmonton HC , Halifax Crescents , Moncton Victorias , Montreal Canadiens , New Glasgow Cubs , Ottawa Capitals , Ottawa Victorias , Port Arthur Bearcats , Smiths Falls , Sydney Millionaires , Toronto Marlboros , Toronto Trolley Leaguers , Toronto Wellingtons , Victoria Aristocrats , Winnipeg Maple Leafs , Winnipeg Rowing Club .