Grant was a member of the Victorias squad that won or retained possession of the Stanley Cup five times between 1895 and 1899 during the trophy's challenge era.

He is regarded as one of the first rushing defencemen in hockey history; Grant used his skating ability to generate offensive chances from his defensive position.

[3] Grant graduated to the senior ranks in 1894 where he made his debut with the Montreal Victorias of the Amateur Hockey Association of Canada (AHAC).

[4] He scored one goal in eight games in 1895 and the Victorias, with a record of six wins and two losses, won the AHAC title, and with it, control of the Stanley Cup, emblematic of Canada's senior amateur championship.

[4] 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.

[3] 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.

[8] 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.