[2] As of July 2023, the assistant principals are Jennifer Howard, Chris Johnston, Rita Skyers, David Granzotto, and Celetta Hunter.

In January 2021, filmmaker Peter Nicks released Homeroom, a documentary following the Oakland High class of 2020 through their senior year.

The 2019–2020 school year started normally but made an unexpected turn in March 2020 as a result of the COVID-19 pandemic, forcing the students into quarantine and to attend virtual classes, with no prom or graduation ceremony.

[citation needed] OHS offers many Advanced Placement (AP) courses and a wide array of challenging academic electives.

Ninth-grade students are parts of learning communities called freshman "families" named after different wildcats such as puma, tiger, panther, jaguar, or lion.

[7] Students in grades 10 to 12 join one of the school's Career and Technical Education (CTE), aligned pathway programs: VAAMP is an art-based academy; it offers classes in art, fashion, drama, and graphic design.

Students are given various tools to prepare themselves for the future, such as community service, college courses, and School-to-Career.

Public health problems involve complex and interrelated social, behavioral, legal, medical and economic issues.

Students are given opportunities for internships in the health profession at Highland Hospital and Kaiser Permanente.

LSJ prepares students for careers in education, law, and community organizations with a focus on social justice and current events.

In the 2008–2009 season, the Oakland High football team managed a 9–2 record, winning a co-league championship.