1908 – 09 Montreal Wanderers season The 1908 – 09 Montreal Wanderers season was the sixth season of play of the Montreal Wanderers . The Wanderers , as defending Stanley Cup champions , defended the Cup against Edmonton before the season started . The Wanderers finished second overall in the ECHA standings and the Ottawa Hockey Club would win the league championship to take over the Stanley Cup . Team business . The Eastern Canadian Amateur Hockey Association league meeting was held November 4 , 1908 and was a pivotal meeting in the evolution from amateur to professional ice hockey leagues . At the meeting the two last amateur , or at least partly amateur teams resigned over the signing of players from other teams . Montreal HC and Montreal Victorias left the league and later would continue as senior level men ' s teams playing for the Allan Cup . Unpaid players would no longer play with paid players . The league would continue with four professional teams . The league name was changed to Eastern Canadian Hockey Association to reflect the change in status . Regular season . Cecil Blachford retired and Bruce Stuart had moved to Ottawa . New additions included Joe Hall , Harry Smith , Jimmy Gardner and Steve Vair . The Wanderers would come close to their rivals , finishing second with nine wins and three losses . On January 25 , Wanderers played an exhibition game in Cobalt , Ontario versus the Cobalt Silver Kings , betting $ 500 on themselves to win , but lost 6 - 4 . After the game Harry Smith would leave the Wanderers to join Haileybury of the Timiskaming League . Highlights . The rivalry between Ottawa and Wanderers continued , Wanderers winning the first on January 6 , 7 – 6 in overtime , with Harry Smith scoring four against his former team . Ottawa would win the next 5 – 4 in Ottawa , and defeat the Wanderers in Montreal 9 – 8 before 8000 fans . Ottawa would finish the series winning 8 – 3 in Ottawa to clinch the championship . Stanley Cup challenges . Montreal vs . Edmonton . Prior to the season , Wanderers would play a challenge against the Edmonton Hockey Club , champions of the Alberta Amateur Hockey Association . Despite all players except for one being a ' ringer ' for Edmonton , Montreal would defeat them 13 – 10 , in Montreal . In game one , Harry Smith scored 5 goals as he lead the Wanderers to a 7 – 3 victory . The Edmontons won game two , 7 – 6 , but Montreal took the two - game total goals series , 13 – 10 . After the challenge , Edmonton would play an exhibition game in Ottawa on January 2 before returning to Edmonton , defeating the Ottawa Senators ( of the FHL ) 4 – 2 . Ottawa played the Toronto Pros the same day in Toronto , losing 5 – 4 . Lindsay , Pitre and Vair , having played with Edmonton for the challenge , would sign after the exhibition game with Renfrew of the Federal League . The players would help Renfrew to the FHL championship . Post - season exhibitions . The Wanderers played an exhibition against Montreal Le National at the Jubilee Rink on March 10 , winning 10 – 9 . The Le National lineup featured several future Montreal Canadiens players including Alphonse Jette , Newsy Lalonde , Jack Laviolette and Didier Pitre . Ottawa and the Wanderers played a two - game series for a $ 1 , 000 purse at the St . Nicholas Rink in New York on March 12 and March 13 . Ottawa won the first game 6 – 4 , and the second game was tied 8 – 8 .