Irvine Robertson was a member of the Toronto Argonauts Rowing Club when he was selected to represent Canada in the coxed eights at the 1908 Summer Olympics. There, alongside Gordon Balfour, Becher Gale, Douglas Kertland, Walter Lewis, Charles Riddy, Geoffrey Taylor, Julius Thomson, and Joe Wright, Sr., he was defeated in the semifinals by the eventual gold medal-winning Leander crew from Great Britain and settled for bronze. Robertson’s greatest prize in the water, however, had come in 1899, when he was awarded the Royal Humane Society’s lifesaving medal alongside his cousin for rescuing drowing people from an overturned boat. In school he also competed in football and hockey, the latter of which he continued into the early 1900s by captaining several teams.
Prior to World War I, Robertson worked for the Bank of Montreal, but he joined the Royal Regiment of Canadian Artillery in November 1914, eventually reaching the rank of Captain and being appointed War Records Officer. He also had a stint with the British Ministry of Information during the conflict and, following the war, began a career as an insurance agent with the firm Greene and Robertson. He later married Ethel Perley, the daughter of Canadian politician George Halsey Perley, and added her family name to his own.