UTS appoints its first headmaster – Henry Job "Bull" Crawford, who also teaches Classics.
UTS opens its doors for the first time, admitting 325 male students. The architectural firm Darling and Pearson designed and built the school, at a cost of $184,383.
UTS produces its first yearbook, The Annals. Over the years, it has had two other names: The Phoenix, and The Twig, which is its current incarnation.
In 1912, UTS establishes Corps number 337 at our school, starting a proud UTS tradition that continued until the early 1970s when it moved to Fort York to become the 337 Queen's York Rangers.
UTS is only four years old in 1914 when its students, alumni and masters began enlisting in the Canadian Forces to fight in the war that was unfolding in Europe. Over the next four years, nearly 400 members of the UTS community would serve in World War I, leading one former student to comment that “if you want to meet a UTS Old Boy, you have to hunt around London or France – not many left in Toronto.” Of those 400 who fought in the war, 63 did not return.
The UTS junior hockey team wins the first Memorial Cup in 1919, the junior hockey championship of Canada. They defeat the Regina Patricias in the span of two games, with scores of 14-3 and 15–5. To qualify as the Eastern Canada representative, they defeated the Montreal Melville by 8–2 in a single game playoff. In the 1910s and 1920s, UTS junior hockey teams played in the Ontario Hockey Association and won the J. Ross Robertson Cup in 1919 and were finalists in 1914 and 1923.
The UTS building expands in 1923, doubling the size of the east wing, with new classrooms, an assembly hall, a gymnasium and a basement swimming pool, which are built by architecture firm Darling and Pearson.
The UTS Rugby team enjoys an undefeated season, winning the Canadian Interscholastic Championship in 1925.
In 1931, the building expands again, along the west wing for teachers in training.
Nearly 1,000 UTS graduates go to Europe to fight in World War II. UTS has a proud tradition of honouring those who served in war with schoolwide Remembrance Day ceremonies.