[23] In 1959, the Santa Clara Union High School District[b] purchased a plot of land to build a new high school, which would be named for thirty-year board member and University of California graduate Adrian Clyde Wilcox.

In an effort to be more welcoming to all students, the school voted to change its colors, mascot, and newspaper and yearbook names.

In 2001, head custodian Joe Miller rediscovered several senior-year panoramic photos while cleaning out a filing cabinet.

After successfully finding photographs for every graduating class, a senior panorama wall was dedicated in November 2003.

[3][39] From 2010 until 2018, Wilcox competed against rival Santa Clara High School in the Black and Blue Olympics (BBO).

[51] During Fantastics week, all of the classes compete against each other in various contests and activities, such as competitive dance and banner painting.

[45] Wilcox High School's campus has an area of roughly 33 acres and spans across the Calabazas Creek.

The campus' quad has over a dozen tables with umbrellas, as well as a couple of grassy hills and a concrete platform.

[2] Wilcox has a Career Technical Education (CTE) Program that covers subjects including business, fashion, and culinary skills.

At the beginning of the fourth quarter of every school year, students with a grade point average of 2.5 or higher are eligible to run for ASB.

[67][68] Wilcox's marching band, the "Black and Gold Regime", has a competitive after-school program and plays at sports games and the annual homecoming parade.

[71] Wilcox High School has a Robotics Club consisting of two teams, each with hardware, software, and business departments.

[73] Wilcox High School has an extensive athletics program, with over twenty teams in sports ranging from football to lacrosse to badminton.

[74] Wilcox's baseball program has won five CIF Central Coast Section titles (2000, 2002, 2004, 2008, 2014) since the turn of the century.