Montreal Victorias
Stanley Cup Champions 1899 "February"

Team Roster
Standing L to R - Jack Ewing, Fred McRobie, J.S. Bishop (honorary secretary treasurer), Frank Howard Wilson (honorary president), Mike Grant, Frank Richardson, Russell Bowie.

Sitting - Cam Davidson, Graham Drinkwater, Hanbury Budden (president), Geordie / Gordon Lewis (goalie), Ernie McLea.

Front - Robert MacDougall.
The 1899 CAHL season was the inaugural season of the Canadian Amateur Hockey League. Teams played an eight game schedule. The Montreal Shamrocks were the league champion with a record of seven wins and one loss. Both the Shamrocks and the Montreal Victorias won Stanley Cup challenges to retain the Stanley Cup for the league.

Montreal received another challenge from the MHA's Winnipeg Victorias. This time, it was decided that they would play a two-game total goals series in February 1899.

The first game was won by Montreal 2–1 on February 15, 1899 at Montreal Arena in Westmount.
Winnipeg's captain Dan Bain injured his eye and did not play in the second game due to hemorrhaging behind the eye.

The second game on February 18, 1899 ended in controversy. With Montreal leading the game 3–2 with about 12 minutes left in the game, Montreal's Bob MacDougall violently slashed Winnipeg's Tony Gingras. As Gingras was carried off the ice, referee Bill Findlay only called Macdougall for a two-minute minor. Angry that he should have been accessed a larger penalty, Winnipeg went into their dressing room in protest. Insulted, Findlay abruptly went home, but returned after officials followed him on a sleigh and persuaded him to return. Once back at the rink, the referee gave Winnipeg 15 minutes to return to the ice themselves. They refused and thus Findlay disqualified the team and declared Montreal the winners.
4,000 people were attending the Winnipeg Auditorium rink to hear returns of the game by telegraph.

The Stanley Cup then passed from the Montreal Victorias to the Montreal Shamrocks as champions of the league March 4, 1899.