The school defeated Montreal Melville by an 8–2 score in a single game playoff to qualify as the Eastern Canada representative at the 1919 Memorial Cup.

[10]: 70  In 1925, Mike Rodden coached the UTS Rugby team to an undefeated season, culminating in the Canadian Interscholastic Championship.

[10]: 34  Prior to the 1960s, the Ontario Ministry of Education required seniors to complete a number of matriculation exams in order to graduate.

[10]: 37 Although matriculation exams would eventually be abolished in the 1960s, UTS students had been calling for change since the late 1930s in the form of valedictory addresses and protests.

[10]: 40  Discontent with the school's inability to reform climaxed in the "Protest for Nothing" in May 1969, which was led by Brian Blugerman, Michael Eccles, Paul Eprile and David Glennie.

[10]: 43  The administration also agreed to allow students to complete their secondary school requirements in 4 years instead of 5,[10]: 43  an advantage that was enjoyed until the 2003 double cohort.

[10]: 65  During his tenure as the premier of Ontario, Bill Davis came under fire for publicly funding UTS, which Liberal education critic Tom Reed called an "elitist" institution.

[10]: 61  In spite of initial concerns about the watered-down quality of UTS boys athletics, the junior girls basketball team won a city title in 1978.

[10]: 27 In April 1993, the New Democratic government of Ontario announced the withdrawal of public funding from the school, leading to a dramatic rise in tuition costs, and prompting the mobilization of all its constituencies to make up the loss.

In 2015, Anand Mahadevan, a teacher at University of Toronto Schools, was the recipient of the Prime Minister's Awards for Teaching Excellence.

[17] In 2023, Isabella Liu, another teacher at University of Toronto Schools, received the Prime Minister's Awards for Teaching Excellence in STEM.

The redevelopment proposal included the construction of a 700-seat auditorium that functions as a university classroom, as well as a double gym, a light-filled atrium and a black box theatre.

[citation needed] UTS has enriched courses and a specialized curriculum,[26] which are designed to challenge and educate at a higher level than at most public and many independent schools.

Because potential UTS candidates are required to pass a rigorous entrance examination to attend the school, its curriculum is accelerated on the assumption that its students assimilate information faster.

[citation needed] UTS's rate of student achievement is commensurate with its selective admissions policy, both in academics and in extracurricular activities.

[27] The school's alumni include 22 Rhodes Scholars [28] and two Nobel Prize winners: chemist John Polanyi and economist Michael Spence.