In its first year, San Mateo High School was located in the Dixon Cottage on Ellsworth Avenue with an enrollment of just 14 students.

Following suit, San Mateo High chose orange and black as its colors, and set its own words to the music of Princeton's school song.

Following a bond election, the Board of Education appropriated $24,000 for the purchase of Brewer Tract, which housed Saint Margaret's School for Girls.

The first graduates of San Mateo High left their school days behind to take part in the leadership of the twentieth century on June 5, 1905.

The students of the first class included Elizabeth Dingwell; Emily Donnelly; Kenneth Green, salutatorian; Freda Hagerup, valedictorian; Eva Leavy; Mabel Moore; and Lena Sullivan.

Women Right's activist Ella Lillian Wall Van Leer would also help create and manage various Art and Architecture departments at the time.

The school board immediately called for a new bond election for $360,000 to be held November 12, 1921; $60,000 was for land and the rest for the building and furnishings.

After a vigorous campaign, highlighted by a mass meeting on November 9, called by Major W. H. Pearson of Burlingame, the issue passed 1710-280.

On November 10, the first anniversary of the laying of the cornerstone, the new T-shaped main building was dedicated and featured the state's most complete science departments with experimental switchboards, fume cabinets, and a greenhouse over the biology rooms; a print shop that handled printing for both high schools and the junior college (now College of San Mateo); a Tudor design library; and a dumbwaiter for fast communication between the principal's office and the superintendent's office on the second floor.

The A-building houses Administration, World Languages, Social Sciences, Photography, Digital Media, Directed Studies, Student Government, Renaissance Leadership, and some English and Mathematics.

The B-building houses just English, with the library occupying the bottom floor; it has a dedicated Media Lab for Journalism and Yearbook.

In addition, the campus has tennis courts; an all-weather football, soccer, and track and field stadium; baseball and softball fields; and a large Main Gym with dance studios built in 2003 that is used for Physical Education courses, dance instruction, after-school sports, and school rallies.

In 2001, the school demolished and entirely replaced the original building in an effort to meet modern earthquake safety requirements.

On February 10, 2006, the campus quad was dedicated to alumnus Merv Griffin, who donated $250,000 to the school ($125,000 of which was intended for the performing arts department).

[7] The Merv Griffin Quad sits squarely in the center of the campus and student life at San Mateo High.

[citation needed] During the 2005 rebuilding process, the original library was recreated, maintaining its signature fireplace and mantel and high ceilings.

Other improvements to the school have occurred since the 2002 Centennial including transformation of the main athletic stadium with all-weather surfaces for football and soccer and an eight-lane all-weather track, remodeling of the swimming pool in 2003–2005, an expanded weight room, and the building of a joint-use Community Gym housing the wrestling and dance rooms and a full-court basketball area.

The second floor boasts a 4,000-square-foot (370 m2) conference room and distance learning facility to host guest speakers and facilitate video conferencing.

In its 2008–2009 run, the paper won numerous accolades at the Peninsula Press Club High School Newspaper Competition.