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Discover the stories and remember the lives of UCC
Old Boys who gave the ultimate sacrifice in the Great War.

Captain Robert Clifford Darling ’04

Died: April 19, 1915

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In a school like ours, where so many interests and activities bring the boys into close relations with one another, there are many opportunities for friendship ; and no friendship formed here (we venture to say) was ever more sincere than that of Trumbull Warren and Clifford Darling. As school boys they were different in several ways. Warren was older, larger, more assertive, and more ready to take the lead in anything; Darling was milder, gentler, more attractive in this sense, and more like a younger brother. But in spite of these differences, or on account of them, they were very fond of each other. They liked being together, always sat together in Form, if it was permitted, and though one was a Day Boy and the other a Boarder, they were almost inseparable. After leaving College, they went to the R.M.C. together, and afterwards each of them entered the family business in Toronto. But apart from business, they had many interests in common and many common meeting places. Finally they went to the war together, one as Adjutant and the other as Assistant Adjutant of the 15th Battalion; and in the end they died almost together, one on the 19th and the other on the 20th of April. It seemed as if Death, which so often separates friend from friend, only sealed their friendship, when the record was perfect and complete.

Robert Clifford Darling was born at Ravensmont, in Rosedale, on May 23rd, 1887, the son of Robert Darling, Esq., wholesale woolen merchant, and came to the College as a Day Boy in 1898. Just at that time his elder brother was one of the heroes of the school, a triple blue, captain of the Hockey team (champions of the Junior O.H.A.), and gold medalist. A younger brother entering College at the time was in danger of being spoiled. But this was not the case with Clifford Darling. He never showed a trace of conceit, and always continued to be a modest and unassuming boy. In 1904 he passed into R.M.C. and graduated in 1907. During his last year at R.M.C. he was a sergeant, and he stood high enough at graduation to be offered a commission in the army. However, he declined the offer and entered his father’s business.

On the day that war was declared he wrote to the Minister of Militia offering his services, and having been appointed Adjutant of the 15th Battalion (48th Highlanders) in the First Canadian Contingent he entered on his duties with enthusiasm, took part in the training at Valcartier and Salisbury Plain, and accompanied the Battalion to France. On March 23rd, while returning from the trenches to Headquarters with Capt. R. Y. Cory, a rifle shot pierced his right lung, and it was some hours before he could be removed to the Field Hospital.

It was at first thought that the wound was not dangerous, but unfavourable symptoms developed after he was removed to London. Sir William Osier and other distinguished medical men attended him, but in spite of all that skill and care could do he died on Monday, April 19th.

Through all his sufferings, which were sometimes very intense, he bore up with great courage, and with his accustomed gentleness and good cheer. His young wife, who was with him during those last weeks, brought his body home for burial. The officers of the 48th Highlanders asked permission to give their ‘late comrade a military funeral, and on Thursday, May 6th, the long procession moved through the streets to Mount Pleasant cemetery. The officers of our Rifle Company and a quota of men took part in the march, along with detachments from all the units in the city. Thousands of people lined the streets or gathered in the cemetery, to show their respect and sympathy for the sorrowing relatives who have lost so much by Captain Darling’s untimely death.

College Times (Summer 1915) pg. 5-6

More information about Captain Robert Clifford Darling ’04 can be found at:

Upper Canada College Roll of Service 1914-1919

The Canadian Virtual War Memorial

“The Red Watch” with the First Canadian Division in Flanders (1916) by Colonel J. A. Currie MP

The Toronto World “Robert Clifford Darling” (April 22, 1915)

Royal Military College e-VERITAS (electronic newsletter)

Commonwealth War Graves Commission

Canada At War

Canadian Great War Project

The Royal British Legion: Every Man Remembered

Imperial War Museum: Lives of the First World War