It is named after pioneer aviator John Joseph Montgomery, who made the first manned glider flight in U.S. history from a hill where the school is located.

On August 31, 2012, a formal ceremony was held to dedicate Montgomery High School's stadium in honor of Al Prazak, a former employee in the Athletics department.

The new principal at that time Lee Romero; took significant action to improve student performance as part of the state system; that "parallels No Child Left Behind, which pushes school to raise test scores."

[16] In 2018, San Diego law enforcement proposed to conduct an active school shooter drill and use it as cover for the arrests of four students.

This tactic, seen as a new and untested law enforcement strategy, was defended by Sweetwater Union High School District officials as a measure to ensure safety.

[17] In 2019, an incident occurred in which a student, dressed in a gorilla costume, was injured by a golf cart after throwing an egg at a staff member.

The market is located in the school's old drama room and also serves as a practical learning environment where students in the transition program can develop job skills and gain work experience.

[21] The market operates as a thrift store on campus, allowing students to select up to three items once per week.

AVID (Advancement via Individual Determination) is an academic course that aids students in preparing for college.

[33][34] A mentorship program where junior and senior students pair with underclassmen to provide academic support and develop a growth mindset.