Montreal Maroons The Montreal Maroons were a professional men ' s ice hockey team in the National Hockey League ( NHL ) . They played in the NHL from 1924 to 1938 , winning the Stanley Cup in 1926 and 1935 . They were the last non - Original Six team to win the Stanley Cup until the Philadelphia Flyers in 1974 and the last NHL franchise to fold , that had previously won a Stanley Cup championship . History . The Maroons joined the league in 1924 along with the Boston Bruins , the first American team . The expansion fees for both teams were $ 15 , 000 , with $ 11 , 000 of the Maroons fee going to their cross town rivals , the Canadiens . At that time , the Maroons were one of two Montreal teams in the league . While the Montreal Canadiens drew primarily francophone fans , the Maroons largely drew fans from the anglophone neighbourhoods of Montreal . The team was designed to appeal to the anglophone fans of the defunct Montreal Wanderers who folded just six games into the NHL ' s inaugural season . The Maroons participated in the longest NHL playoff game of all time , losing 1 – 0 to the Detroit Red Wings in 176 : 30 of play ( 16 : 30 of the sixth overtime period ) on March 24 – 25 , 1936 . Financial strains from the Great Depression led the NHL to realize that Montreal , despite its size , could not support two NHL teams . While both the Canadiens and Maroons had trouble drawing fans , there were far more francophone supporters for the Canadiens than there were anglophone supporters for the Maroons . As a result , the Maroons finished with the worst attendance in the league for three seasons in a row . This , along with the fact that both teams were owned by the Canadian Arena Company by 1935 ( Ernest Savard and Maurice Forget , who owned the Canadiens , were part of the Canadian Arena Company and so were the owners of the Maroons , James Strachan and Donat Raymond . ) made it obvious only one team could represent Montreal . The financial strains of the Maroons caused them to sell off star winger Hooley Smith and others . Despite the Maroons ' financial troubles , they continued to play competitive hockey well into the 1930s . In fact , the Maroons team that won the Stanley Cup in 1935 were the last team to do so without a loss in the playoffs for 17 years . However , the team ' s bleak financial situation finally caught up with them in 1937 – 38 , as they finished 12 – 30 – 6 , the club ' s worst season since winning only nine games in 1924 – 25 . The league allowed the Maroons to suspend operations for the 1938 - 39 season . The Maroons ' owners tried to sell to interests in St . Louis , Missouri . Earlier in the decade , St . Louis proved that it could support NHL hockey when the Ottawa Senators moved there to become the Eagles . However , while the Eagles had drawn very well , they only survived one season due to the high costs of travelling to Boston , Montreal and Toronto . The league was not about to give St . Louis another chance given the economic situation of the time . The Maroons were eventually sold to interests in Philadelphia , who had every intention of reviving the team after World War II . However , in 1946 , the NHL reneged on long - standing promises to reinstate the Maroons and New York Americans . Len Peto , a director with the Montreal Canadiens , took control of the dormant Maroons and succeeded in getting the franchise transferred to Philadelphia , but lack of a suitable arena was the problem and the league gave Peto until the end of the 1946 – 47 season to rectify this . By that time , the franchise could not build a suitable arena , and this was the end of the dormant franchise . Well - known players included Nels Stewart , Hooley Smith , Babe Siebert , Clint Benedict , and Alex Connell The last active Maroons player was Herb Cain , who remained in the NHL until 1946 . The Last Game . The Maroons ' last game was played on March 17 , 1938 , at the Montreal Forum against the Montreal Canadiens . The Maroons were the home team . The game was meaningless for the Maroons . They were finishing last in their division and out of the playoffs . The Canadiens scored the only goal of the first period and then jumped into a 4 - 1 lead by the end of the second . In the third period the Canadiens added two more goals . With the game out of the Maroons ' reach , Jimmy Ward scored at the 10 : 40 mark of the third period and then added one more with eleven seconds left in the game - and in the Maroons ' career . The final score was 6 - 3 for the Canadiens . Only about 5000 people attended . Season - by - Season record . All Time Win - Loss Record : 271 – 260 – 91