On February 21st, President Quinn of the National Hockey Association, announced that the trustees of the Stanley Cup had received a challenge from the Maritime Hockey League on behalf of the winner for the 1914 season.  President Quinn quickly announced that the Maritime challenge was accepted and would take place previous to a challenge put forth by the Pacific Coast league.  President Quinn left Montreal for Toronto to meet with NHA champion Toronto Blueshirts team in order to make arrangements for the upcoming games.  With the prospect of playing in a second Stanley Cup challenge series, the Millionaires management started to become concerned with their own team finances.  Several times during the year, the Sydney team was forced to hand over money to the other teams in order to allow these teams to fulfill their games in Sydney.  At this late point in the year Sydney's coffers were getting low but  the city and management was still committed to sending the Millionaires to Toronto for the challenge if they did win the league's standings.  They were motivated by the general opinion that if Sydney was able to win the Stanley Cup it "would be the greatest advertisement the city had ever received".

On February 29th, President Quinn of the NHA, announced the dates of the Stanley Cup challenge matches to take place between the NHA champion and the MPHA champion.  Those dates were scheduled for March 9th and 11th and would take place in Toronto.  The winner of this series of games would then be slated to play the PCHL champions in a second Stanley Cup challenge series.