Day enjoyed a 33-year career as a player, referee, coach and assistant general manager, 28 of which were spent in various capacities with the Maple Leafs.

Legend has it he would often walk from Port McNicoll to Midland (approximately three kilometres away) in the winter, for games at the town's Casino Rink.

[1][2] He played for the Hamilton Tigers of the Ontario Hockey Association in 1922–23 and 1923–24 then joined the varsity team at the University of Toronto, where he was enrolled as a pharmacy major.

He played left wing in his rookie season and then switched to defence, where he would remain for the rest of his career.

While still playing for the Leafs, Day became coach of the West Toronto Nationals OHA junior team and led them to a Memorial Cup victory in 1936.

[citation needed] Day retired to enter business life, running Elgin Handles in St. Thomas, Ontario[4] until selling it to his son in 1977.

Day was almost convinced by Jack Kent Cooke to become the first general manager of the Los Angeles Kings in 1967, but he decided not to take the job, recommending Larry Regan instead.