Edited from Wikipedia entry:

Lord Stanley of Preston as Governor General of Canada became highly enthusiastic about ice hockey. Stanley was first exposed to the game at Montreal’s 1889 Winter Carnival, where he saw the Montreal Victorias play the Montreal Hockey Club.

Stanley’s entire family became active in ice hockey. Two of his sons, Arthur and Algernon, formed a new team called the Ottawa Rideau Hall Rebels. Arthur also played a key role in the formation of what later became known as the Ontario Hockey Association (OHA), and would go on to be the founder of ice hockey in Great Britain.

Arthur and Algernon persuaded their father to donate a trophy to be “an outward and visible sign of the hockey championship”. Stanley sent the following message to the victory celebration for the three-time OHA champion Ottawa Hockey Club:

“I have for some time been thinking that it would be a good thing if there were a challenge cup which should be held from year to year by the champion hockey team in the Dominion [of Canada].

There does not appear to be any such outward sign of a championship at present, and considering the general interest which matches now elicit, and the importance of having the game played fairly and under rules generally recognized, I am willing to give a cup which shall be held from year to year by the winning team.

I am not quite certain that the present regulations governing the arrangement of matches give entire satisfaction, and it would be worth considering whether they could not be arranged so that each team would play once at home and once at the place where their opponents hail from.”

As regular season champions of the CAHL in 1899, the Dominion Hockey Challenge Cup (known today as the Stanley Cup) was to awarded to Montreal Shamrocks. But before the Shamrocks were crowned cup champion, the Montreal Victorias (1898 cup champion) played and won a cup challenge against the Manitoba Hockey Association (MHA) champion Winnipeg Victories. The result of the matches was:

February 15, 1899 – Montreal Victorias (CAHL) 2–1 over Winnipeg Victorias (MHA) in Montreal.

February 18, 1899 – Montreal Shamrocks (CAHL) 3–2 over Winnipeg Victorias (MHA) in Montreal.

After defending the Challenge Cup, the Montreal Victorias did not win the CAHL regular season championship, which was instead won by the Montreal Shamrocks.

The Shamrocks then accepted one challenge by the Ontario Hockey Association (OHA) champion Queen’s University. The result of the match was:

March 14, 1899 – Montreal Shamrocks (CAHL) 6–2 over Queen’s University (OHA) in Montreal.

Dominion Hockey Challenge Cup to December 31, 1899
Team Start End Challengers # of days total days
Montreal Victorias (AHAC) January 1, 1899 March 3, 1899 CAHL loss 62 1,136
Montreal Hockey Club (AHAC)          – 720
Winnipeg Victorias (MHA)          – 320
Montreal Shamrocks (CAHL) March 4, 1899 December 31, 1899 CAHL win; Defeated OHA 303 303

There are actually three Stanley Cups in existence:
1) Stanley’s original Cup from 1892, known as the “Dominion Hockey Challenge Cup” was awarded until 1970, and is now on display in the Vault Room at the Hockey Hall of Fame in Toronto.
2) In 1963, NHL president Clarence Campbell believed that the original Cup had become too brittle to give to championship teams, so the “Presentation Cup” was created and is the well-known trophy awarded today.
3) The final Cup is a “Replica Presentation Cup”, which was created in 1993 by Montreal silversmith Louise St. Jacques and is used as a stand-in at the Hall of Fame when the Presentation Cup isn’t available.

Unlike other major league sports trophies, a new Cup isn’t made every year. Instead, after each championship, the names of the players, coaches, management, and staff of the winning team are added to the Cup. The first team to have its roster engraved was the 1906-07 Montreal Wanderers, whose names were etched within the inner bowl of the Dominion Hockey Challenge Cup. The only other team names engraved on the inner bowl are the 1914-15 Vancouver Millionaires.

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