Originally situated above King Edward Public School (Jr. & Sr.), in 1911 architect Charles Hartnoll Bishop[2] completed the permanent location opened at the corner of St. Clair Ave. West and Oakwood Avenue in Collegiate Gothic structure.

Oakwood's population studies in a three-storey building and has a gym, weight room and art department located in the basement.

During the last stretch of the Ontario New Democratic Party government of Bob Rae, Oakwood was next on the list of schools to be renovated, directly after Riverdale Collegiate Institute.

After Rae had lost the 1995 provincial elections to the Progressive Conservative Party of Ontario under Mike Harris, the plans for renovation were scrapped.

Oakwood followed a four-day "block" cycle, although due to its status as a non-semestered school, classes were shorter and occurred more frequently.

The team won the (TDSSAA) Toronto high school senior boys basketball championship for the 2014-2015 season.

Previous locations have included Beijing, China; Ålborg, Denmark; Los Angeles, California; Yellowknife, Northwest Territories; Paris, France; Rome, Italy; Athens, Greece; Vienna, Austria; Prague, Czech Republic; New York City, New York; and Chicago, Illinois.