There were several games that were played between 1886 to 1892 that involved the top five senior amateur teams in the country (Ottawa, Quebec & three in Montreal). The results of these games have been lost to the annals of time.

  On Dec. 15, 1892, a special league meeting was held to draw up a schedule to play for a new trophy that Lord Stanley of Preston (Governor General of Canada 1888-1892) had presented to the league. The schedule consisted of eight games; each team playing each other twice (one home, one away) and remained that way until the league's demise in 1898. The champion of the league was not only awarded the Senior Championship Trophy, but also had a chance to challenge against other leagues in the Dominion for the new Stanley Cup. Play was to begin on Jan. 7,1893.

  The first regular season game ever played involved the Ottawa team (known as the Generals by some historians-later to be known as the Senators) versus the Victorias of Montreal. The Montreal Vics won this game in front of a home crowd. The defeat would prove costly for the Ottawans. They finished the season at 6-2. The Montreal Winged Wheels (also known as the triple A's) finished at 7-1. The Ottawa team also played in the Ontario Hockey Association (OHA) in 1893 and the newly elected trustees of the Stanley Cup ordered Ottawa to play Toronto's Osgoode Hall hockey club in Toronto. Osgoode Hall won the OHA championship that year and had beaten the Ottawans in OHA play. Ottawa refused this match and the first Stanley Cup was awarded to the winged Montrealers, champs of the top senior league in the Dominion, without a playoff game.

  The first playoff game in the league and in Stanley Cup history occurred on March 17, 1894. At the end of the 1894 schedule, a tie had resulted between four teams (Winged Wheelers, Vics, Ottawa & Quebec). Again, the trustees were put to the test to break the tie and, unknown to the teams at the time, the winner of the Stanley Cup. A special meeting was held on March 10, 1894 to resolve the issue. After much debate, the Ottawans were scheduled to play the Victorias in Quebec, the Wheelers were to play Quebec in Ottawa and Montreal was chosen to host the final. The Quebec team disagreed with this format. They believed that the final should be played on the home ice of the victors in the first games. The trustees stuck to their plan. Quebec, in protest, withdrew from the playoff. This is the closest that this Quebec club ever got to the Cup. The Wheelers were ordered to play the rival Victorias and the winner would play Ottawa. All the games were to be played in Montreal. The Wheelers won the game 3-2 then defeated the Ottawans 3-1 on March 22, 1894 to win their second Stanley Cup. No other challenges were accepted by the trustees in that year.

  Other leagues continued to challenge for the Cup and were accepted. Queen's University in Kingston, Ont. (OHA) challenged in 1895 and the Winnipeg Victorias of the Manitoba & Northwest Territories Hockey League challenged and won the Stanley Cup away from the AHAC in February of 1896. The AHAC got the Cup back in December of that same year and once again was the top amateur league in the Dominion until the league folded in 1898.

Criticism of the league began to develop in the press in 1894 & 1895. This was due to the start of games being delayed. A fan would have to pay up to a dollar for reserve seating only to wait in the cold for an hour or two for the action to begin. The only heated areas of the arena were confined to the dressing rooms and the bathrooms. Still, it was not uncommon to see over four thousand people at a game. The newly appointed Governor General and his staff regularly attended matches. Lord Stanley, by this time back in England, never did see a game played for his trophy.

  Controversy stuck again before a game on February 2, 1895 in Quebec. The Montreal Crystals were floundering and tried to merge with another club that played in the Montreal Amateur Athletic Association (MAAA), the Montreal Shamrocks. The Quebec club protested to the league and it was upheld. The game became void and the Crystals were fined. Then, on February 23, 1895, more controversy surrounded the Quebec team. An extremely rough match was played between Ottawa and the host Quebec squad. Ottawa won the game 3-2, but the unruly fans pursued the exiting officials and dragged them back to the rink to declare the game a draw due to the unsportsman-like play of the Ottawans. Things got so out of hand, that the police were called in to break up the protest. An emergency meeting was held on February 27, 1895 to dole out the punishment. Quebec was suspended for the remainder of the season. The Quebec newspapers expressed their anger at the league for such a harsh sentence, claiming that the Ottawans instigated the whole incident. At the start of the 1896 season, an apology was given to Quebec and they were re-admitted into the league. Also, in that same year, the struggling Crystals were allowed to merge with the Shamrocks.

  The league was always considered the top league in the continent, if not the world until 1898 when inner turmoil forced the league to disband. A rule stated that no intermediate team could join the senior circuit unless they won their respective championship. The Ottawa Capitals of the OHA (Ottawa District) tried to suspend this rule during a meeting on December 11, 1897 to gain admittance into the league. This motion was declined. A year later, during a meeting on December 10, 1898, a second attempt was made to admit the Capitals. This time, the motion was passed. In response, Quebec, the Victorias and Ottawa withdrew from the league. the Winged Wheels asked the league to reconsider it's decision. The answer was a flat out 'no' and the Montrealers resigned. The delegates from these teams met on the same day at the Windsor Hotel in Montreal and formed their own league. They adopted the constitution of the AHAC and named their new league the Canadian Amateur Hockey League (CAHL). The Montreal McGills of the MAAA applied for admittance into the new league but so did the Montreal Shamrocks. The McGills withdrew their application to make way for the Irish.