[5] It was named for Raymond B. Leland, who had served as principal of San Jose High School, and his son Gordon Leland, who had been a student at the school and had died in World War II.

[6][7] Leland has won accolades for its speech and debate team,[8] and more recently its FIRST Robotics Competition Quixilver 604[9] and its FIRST Tech Challenge Quixilver 8404[10] robotics teams.

[11] In 2021, U.S. News & World Report ranked Leland as the number 1 high school in San Jose Unified School District and number 68 in the state of California,[12] and the education ranking and review website Niche ranked the school as the number 1 high school in the district and number 77 in the state.

[13] In 2014, Leland was ranked number 20 in the United States for high standardized test scores between 2012-2014.

[14] Newsweek ranked Leland High School 54th in the nation.