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Oswald George Shepherd attended TCS from 1907-1910. His father was E.H. Shepherd, Esq. from North Bay, Ontario. He played First Football and Hockey while he attended the School. He served in both WW1 (Lieutenant with the 159th Battalion Canadian Infantry) and WW2 (Lieutenant-Colonel and District Dental Officer in the C.D.C. at M.D. 7).