Amongst the teams Smaill played for were the Cobalt Silver Kings, Ottawa Senators, Victoria Aristocrats, and Montreal Wanderers. He won the Stanley Cup with the Montreal Wanderers in 1907 and 1908.
On Dominion Day 1909 Smaill narrowly escaped a similar death to that which befell his former teammate on the Montreal Wanderers Hod Stuart two years prior in 1907. Smaill dove into shallow water outside the Cartierville neighborhood in Montreal to recover a pair of glasses which had been dropped from a boat. When he came up to the surface his face was covered with blood and he was badly stunned.
Smaill was a useful utility player. Outside of the forward left wing position he was also occasionally used as a cover-point (offensive defenceman) because of his strong rushing ability.

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