Here is a compilation of the available Montclair High School class portraits from 1883 to 1919, the latter being the year just before the first Amphitheatre. From 1916 to 1919, the class portrait was taken at the front entrance of the present Main Building rather than in the Amphitheatre, which was customary in the early yearbooks, likely because the Amphitheatre was still under construction. All of these photographs have been retrieved from the Montclair Public Library Local History Collection and have been adjusted for improved clarity.

These files contain stunning architectural drawings, newspapers, and photographs relating to the buildings of Montclair High School. The current Main Building was initially designed as a larger replacement to the original high school building that was located on the site that is now the field of Hillside Elementary School. Construction began on June 29, 1914, with the building's first senior class graduating in 1916. Eventually, the student body became too sizable, and the district contracted Montclair-based architect Alfonso Alvarez to design a massive expansion for the Main Building. Completed in the 1960s, this expansion included the addition of the auditorium and gymnasiums, which were both significantly larger compared to their original counterparts.

A plaster copy of the Discobolus used to stand proudly in the Montclair High School lobby, and it was difficult to miss. Now, the imposing Classical Greek sculpture is no longer present in the Main Building entryway. So what happened to it? This file includes two articles published in The Montclair Times. The first is the documentation of the statue initially being gifted to the school in 1914 (this was before the high school had moved to the current building). The second is an investigative report conducted in 1961 with the intent of finding out the whereabouts of the Discobolus, which, at the time, had mysteriously vanished about fifteen years earlier. To say the least, the statue does not have a fortunate ending.