[citation needed] Brentwood High School began with the Ross Building, with its tennis courts and state-of-the-art swimming pool.

In 1961, Eugene G. Hoyt, then the District Principal, and Raymond Scheele of Hofstra University presented a plan for curriculum development to Dr. Meade of the Ford Foundation.

On the basis of this work, the foundation awarded Brentwood High School (with Hofstra as the "cooperating university") a grant of more than $300,000 for curriculum development.

During the summer of 1968 (in compliance with the Architectural Barriers Act of 1968), temporary portable classrooms were constructed between the Ross and Sonderling Buildings, housing the language and health classes.

[2] On January 11, 1968, then-Senator Robert F. Kennedy visited Brentwood High School and spoke to 800+ students, parents and faculty in the Sonderling auditorium.

[3][4] On June 27, 1971, the last Brentwood senior class graduated together as one 1,400 body of students enjoying the now demolished Commack Arena as the commencement site.

The initial output of WXBA was ten watts, which meant that the signal barely made it three miles from the school under some conditions.

Brentwood High School established an Air Force Junior Reserve Officers' Training Corps (AFJROTC) in 1977.

[9] WXBA moved to expanded facilities in the newly built G. Guy DiPietro Learning Center[10] during the 1988-89 school year.

[15] On Veterans Day 2005, Newsday covered the dedication of a memorial to 15 graduates of the high school who had died during the Vietnam War.

[17] On October 28, 2012, the Green Machine Marching band took second place at the Syracuse Carrier dome in the division Large School II with a score of 89.05, performing its program "Conflict Without Resolution".