A late season challenge from the Winnipeg Victorias saw the Montreal Shamrocks play three games against the Manitoba champions. Playing all three games in five days, the Victorias won the first one, and the Shamrocks claimed the other two to remain Stanley Cup champions for another challenge. All three games were decided by one-goal margins. Montreal's Harry Trihey was the offensive star with seven goals, including three in the finale.
Following the conclusion of the 1900 season, Montreal accepted a challenge from the Halifax Crescents of the Maritime Hockey League. In two games, the Shamrocks convincingly defeated Halifax by a combined total of 21-1. Montreal forward Arthur Farrell set a new Stanley Cup record by recording four goals in each of the two games.
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