It was far back from the street, and was very long and thin, likely built similar to the Bristol Elementary School building.

The high school building was completed in 1907, while businessman Robert A. Holekamp briefly served as district superintendent.

Some time in the 1940s or 1950s, an autobody shop was built in the northeast corner of the high school property to serve auto maintenance classes.

It was constructed as a separate building that could house small cars or large semi trucks.

[10] The main entrance of this building was on the ground floor facing Bradford Avenue and led into the cafeteria.

[7] WGHS was racially integrated in 1956, 2 years after Brown v Board of Education, bringing in children from Douglass High School.

In 1966 a 2-story elevated wing was added onto the back of the building, containing many classrooms for math and world languages.

[12] In October 2002 a white powdery substance found in a tissue box provoked a two-hour lockdown.

At this time, the old auto maintenance shop and a small original north wing was torn down to make room for it.

A temporary auto maintenance shop was set up under the 1966 section of building, where the plywood walls still stand, as of 2024.

It included new classrooms, state-of-the-art science labs, a main band room, private band practice rooms, art studios, industrial technology classrooms, and an autobody shop in the basement.

The expansion was built to resemble the look of the existing building, including the use of terrazzo floors and steps, and limestone accents.

[15] The old gymnasium behind Knight Auditorium was sectioned off during this process and since contains the drama department rooms, as well as a black box theater.

It was built for $2 million, funded by Mr. and Ms. Frick, and was designed to be a clean theater, meaning nothing will be painted or drilled into the floors for performances, unlike the Knight Auditorium.

The Webster Groves High School building has approximately 130 classrooms along with an auditorium, a media center, and a theater.

As of 2024, it is undergoing a full transformation, including an eight lane track, turf field, concession stands, locker rooms and restrooms, concrete seating, and a video scoreboard.

A number of festivities surround the game, including a shared dance and a separate bonfire and pep rally at each school.

In 1999 Time magazine devoted a cover story to a week at Webster Groves High School.