Oak Bay High School is renowned for its outstanding academic, artistic and athletic accomplishments, a tradition of excellence that has been built over many years by the talents and efforts of students, teachers and administrators. Many Oak Bay students have distinguished themselves in business, the arts, the professions and public service.

Oak Bay's first high school was built in 1915 on Oak Bay Avenue where the Municipal Hall is now located. The Cassanave farm on Cranmore Road was purchased in 1919 for future expansion. It wasn't until February 1929 that construction of a frame building including 12 classrooms, an auditorium, lecture halls, science laboratories and an art room was completed. The principal, Mr. J. M. Billings, had the honor of moving 250 pupils into the new building.

In 1951, more space was needed and construction of a junior high school with space for home economics and industrial education began across the field from the 1929 building. When it opened in 1953, there were 252 students enrolled in grades 7 and 8. As the population grew, reaching 2,000 by 1967, additions were made to both buildings. A new wing and gym were added to the senior school, and an auditorium and gymnasium to the junior high building. The construction classes from three Victoria high schools built the band room outside the junior school in the 1960's. As population growth slowed, the number of students attending the schools declined and, for this reason, the two schools were amalgamated during the early 1980's. As of 2019, Oak Bay is the largest high school in Victoria and enrolls about 1300 students in grades 9-12. Included in this number there are approximately 130 International Program students who board with local families and pay tuition in order to study in Greater Victoria.

The school has been through many changes, but one aspect has remained the same: Oak Bay High School is still committed to excellence.
(Adapted from Gillian Fosdick, 1972)