Here’s the full skinny on the cup, as my last message was largely from memories of cup stories, and this is th efull story from http://www.nhl.com/history/index.htm is as follows:
The original cup was silver, was 7 1/2 inches tall and 11 1/2 inches across and cost ten guineas (50 bucks) in 1892 when it was purchased by Lord Stanley. The official name for this cup was The Dominion Hockey Challange Cup, though it was known colloquially as “The Ten Guinea Cup” The silver rings were there from the beginning, though originally only the team names were engraved. The holder of the cup was in possession of it until it lost it in a challenge match, at which point it had to return the cup to its trustees “in good order”
Originally, players began carving their names into the silver ring useing a knife or a nail or whatever sharp object was handy at the time. The original ring was replaced by a “cigar shaped” base in 1939. The cigar base was retired in 1948 and was replaced by a removable base attached to the bowl by a collar. In 1958 the modern one-piece cup and base was introduced, and in 1969 the bowl was replaced since the original bowl was becoming brittle and too delicate to be handled.
The cup, though it was intended to be awarded in 1892, was not given away that year. The original cup trustees, against Lord Stanley’s wishes, refused to give the cup to the Ottawa amateur team, considered by many to be the best team of the day unless they played a match for it. Ottawa refused to play Toronto, the chosen team, and instead withdrew from the Ontario Hockey Association. The Montreal AAA team agreed to step up and play the match in 1893, they won, and became the holders of the first cup.
In 1894, the first playoff was held, a three-team round robin affair once again won by the Montreal AAA. The original cup was determined by “challenge” much like current boxing championships. Any team in Canada could enter the playoffs, which occured generally twice every hockey season. The first western team to win the Cup was the Winnipeg Victorias, who won it from the Montreal Victorias. The longest trip a team ever made was the 1905 Dawson City Klondikers team who made the 4,400 mile trip to Ottawa to challange the Silver Seven for the cup. To arrive, the team took dogsleds to the coast, a boat to Vancouver, and a train to Ottawa.
Also in 1905, a member of the Ottawa Silver Seven left the cup in the Rideau Canal overnight. It got there when a player was challeneged to dropkick the cup. Drunk but confident he did, and succeeded in kicking the cup into the canal, where it was left until the hungover players realized the next morning what they had done and returned to retrieve it.
The cup was not awarded in 1919 due to an outbreak of the Spanish Flu, leaving the two teams in the finals decimated by disease. The Montreal Canadiens, the NHL champs, and Seattle Metropolitans, the PCHA champs, were tied 2-2-1 when so many players became hospitalized that the championship was called a draw.
In 1925, ten players of the Hamilton Tigers, which was supposed to play in the finals, went on labor strike. Players recieved no extra pay for playoff games, and the entire hamilton squad, regular season champs went on strike, pehaps one of the earliest sports labor disputes known.
Hope that was enough trivia for one day!