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".
Blogs about the Sydney Millionaires Professional Hockey Club and their 1913 Challenge for the Stanley Cup.
Upsetting news came out of New Glasgow in late February that the Black Foxes were in serious financial trouble and it was a possibility that the team would not be able to finish the 1914 season. In response, the New Glasgow management reached out to President Larder of Sydney and requested some financial support. President Larder promised that Sydney would pledge 150 dollars per game in Sydney. The New Glasgow players had not been paid by the team management and were ready to walk but were brought back to the fold after a win against the Halifax Crescents and the increasing possibility of winning the Crosby Cup. The players agreed to stay and take their salary from whatever was brought in at the gate. N. W. Mason, a New Glasgow business man and rink owner, took over operation of the team and began to organize local benefits in New Glasgow. One event took place at the theatre and a second one at the arena. Mason was hoping to get enough money together to fund the team for the rest of the season.
February 1914 brought news of player changes as the Millionaires adjusted to make a run at the Crosby Cup. On a trip to Halifax, Teddy Turner, who spent most of the season playing in the spare role, was called back to Montreal due to a sickness in his family, Teddy was unable to return to the team. Sydney fans were delighted to hear that Joe Tetrault was returning to finish the 1914 season with the Millionaires. Tetrault, after the incident in Sudbury earlier in the season, headed back to Montreal where he played in a few games with the Montreal Wanderers of the NHA before being resigned with Sydney. A few days later the Millionaires signed a second player, Ray Mallen. Mallen was released by the Halifax Crescents and was quickly grabbed by Sydney. Ray hailed from Morrisburg, Ontario and had played for a short time with the Quebec Bulldogs in an exhibition series against the Victoria Aristocrats of the PCHA after the Stanley Cup matches of the previous year. Ray Mallen came from a hockey family. His two brothers Jim and Ken Mallen were also playing professional hockey. His brother, Jim had previously played in Sydney as an amateur in the Cape Breton Senior Hockey League. Shocking news came the next week when it was announced by the management that Billy Dunphy, a popular local boy, was released by the Millionaires and had signed on with the New Glasgow Black Foxes. A local sports reporter summed up the disappointment of this news with the following rhyme:
The Millionaires went on a winning streak over the next month; winning six of their eight games and were able to tie the Halifax Crescents for the lead in the MPHA. The two teams met on January 28th with the winners poised to take over the league lead. Robin Foote, the local boy was given his first game in goal replacing Joe Savard who was out with a sprained thumb. At the end of regulation time, the game was tied at five to five. The game was characterized as a very fast and clean game but as the game went into overtime, it began to get rough. During the opening play of the second overtime, Ken Randall got the puck on a pass from Harvey Richardson and eluded Andy Kyle for a direct line to the Crescent's goaltender. Andy Kyle turned and threw his stick and knocked the puck away from Randall. The referee blew his whistle and called a five minute penalty for throwing of a stick. According to Sydney papers, Kyle then skated away from the ref and leaned on the goal refusing to go to the penalty box. Referee Brown and Ken Randall skated over to Kyle where the ref was able to convince Kyle to leave the ice. On the way to the penalty box Kyle skated up to Randall and punched him on the jaw, knocking him to the ice. Sydney's Mayor, A. D. Gunn, who was in a box near the scene, jumped up and ordered Sydney's chief of police to arrest Kyle for assault. At that point, fans of the Millionaires piled onto the ice and along with a few of the Millionaires players attempted to get at Kyle. Kyle's New Glasgow teammates were able to protect him until two policemen were able to get him off the ice. Kyle was then taken to his hotel room at the King George Hotel accompanied by four police officers and allowed to change out of his hockey gear before being taken out to a waiting carriage staffed by two more officers who took him to the jail for the night. The Millionaires were the eventual winners of the game due to a goal scored by Billy Dunphy.
In response to the Quebec Bulldog's defiance of the NHA's decision to suspend Harvey Richardson and to send him back to Sydney, a rumor arose that the Millionaires were going to offer Quebec star Joe Hall fifteen hundred dollars to sign a contract with Sydney. This was in obvious violation of the NHA/MPHA agreement but since the Bulldogs were not releasing Richardson, the executive felt that they were justified. Shortly after this rumor was published in the press, it was announced that the Bulldogs had finally let Richardson go and he was on his way back to Sydney to join the Millionaires.