The AHAC disbanded in 1898, and the Victorias moved to the newly formed Canadian Amateur Hockey League (CAHL) for the 1899 season. Grant scored two goals in seven games in CAHL play. During the season, Grant and his teammates fielded another Stanley Cup challenge from the Winnipeg Victorias. They retained the trophy following a two-game series; it was Grant's fifth and final Stanley Cup win. Grant was offered a professional contract in New York that was worth the equivalent of $3,500 per year in the earl 1900s, but opted to remain in Montreal. After playing the 1900 CAHL season with the Victorias, he was loaned to the cross-town Montreal Shamrocks in 1901 as an emergency replacement for Frank Tansey. Grant appeared in two league games, and two Stanley Cup challenge games for the team before returning to the Victorias for a final season in 1901.