During the 1950s, all Wakefield students were white, in accordance with Virginia's laws requiring racial segregation in public schools.

[5] The original building, which was located at South Chesterfield Road, was built in 1952 and was opened for the 1952-53 school year.

In 2007, the county's school board began the planning process for modernization or replacement of the Wakefield building.

Wakefield offers many opportunities for students to participate in various clubs and activities to support their academics and challenge them to learn and grow outside the classroom.

Stories covered include local and international news, school events, performing arts, athletic development, and the ever-popular "Kiss-O-Gram" (student-to-student messages on Valentine's Day).

Wakefield sponsors a team of students to participate in the locally televised quiz show, It's Academic.

The Warriors have sent the team to Scholastic Bowl tournaments (in addition to It's Academic) and have come home with multiple National District titles.

Wakefield's Academic Cohort Program identifies African American and Hispanic males in 9th grade who are capable of taking a more demanding courseload.

They meet weekly with a Coordinator, a school counselor, and social worker to lend support to each other as they tackle the demanding coursework.

Students go to these labs in an effort to develop their academic lack in the content area (i.e. make up tests, get homework assistance, or study).

The Arlington Career Center[7] offers technical courses in Business & Communication, Industry & Engineering, and Health & Human Services.

Wakefield encourages students to take Advanced Placement courses, favoring "preparedness" over intelligence and finesse.

The "AP Network", which began as an Exemplary Project approved by the Arlington County School Board in the spring of 2004, is rooted in this belief.

Since the inception, the faculty and staff of Wakefield have been "networking" and creating numerous academic programs to introduce pre-AP and AP courses.

At the start of the seniors' academic year, students select a date in which they are to present the project, giving them a time frame in which papers are to be submitted.

During the year, the student then decides on a panel (composed of one pre-determined faculty member, one expert in the field, one person from the community, and another fellow senior) who will grade the project.

This was the first time in the history of Wakefield Warrior athletics that the two sports, softball and baseball, were played on different fields.

On March 7, 2011, President Obama revisited the school, this time with the Australian Prime Minister Julia Gillard and the United States Secretary of Education Arne Duncan.