The Montreal Victorias were challenged for control of the Stanley Cup by the Winnipeg Victorias in February 1896, and lost the trophy by a 2–0 score in a one-game playoff. Montreal regained the Stanley Cup in December of that year, defeating Winnipeg 6–5. In AHAC play, Grant scored three goals in eight games in both the 1896 and 1897 seasons. He captained the Victorias to a successful defence of the Stanley Cup in 1897 and the team retained the trophy in 1898 by virtue of winning the AHAC title.