Students are introduced to increasingly challenging and probing academic course work, enrichment in the arts, music, and physical education, and are taught a strong foundation in study, research and computer skills. English, mathematics, history, and science are a part of the core academic program in Grades 5-8. Students begin their foreign language study in the Grade 6 with semester introductory courses in Spanish and Latin, and then pursue one language in greater depth in Grades 7 and 8. After mastering the introductory skills of the elementary years, students are ready to develop more disciplined methods of organizing their time, pursue their subjects in greater depth, and take on a more active leadership role in the school. The middle school program provides many exciting new opportunities to do so.

• Departmentalized Program: Fifth grade is a transition year where students have core teachers for at least three subjects in addition to specialists in history, science, music, art, computer, religion and PE. In 6th, 7th and 8th grades, students are involved in a fully departmentalized program, traveling from teacher to teacher for all of their subjects and are assigned a locker.
• Advisory Program: All middle school students are assigned to a grade level advisory team of twelve students and a faculty advisor. These groups meet three times a week, plan school-wide activities, form action-teams for school projects, set goals, and review individual academic progress. Advisories provide each student with a faculty advocate and advisor to assist him or her in academic, social and emotional growth.
• The Language Arts Resource Center: This serves as the English classroom for Grades 6, 7, and 8. The teaching of writing is enhanced by the availability of computers for every student in the class, allowing each to write every day on a word processor. The language arts curriculum provides a balanced instructional program in literature, vocabulary development, and grammar, as well as formal and creative writing.
• Mathematics and Science Programs: Beginning in Grade 5, the mathematics program offers an accelerated track preparing qualified students for Algebra I in the Grade 8. Lab-centered science courses in a new state-of-the-art facility feature hands-on investigations in biology, chemistry, physics, and environmental science. With computers linked to video microscopes and the Internet at each lab station, students are able to do hands on research in science.
• Fine and Performing Arts: Instruction in music, drama, and art is considered an integral part of each child's education. It seeks to draw out the creativity in every child, while exposing them to a multitude of media and providing them with performance opportunities. With the recent opening of the Sprague Center, students have the opportunity to perform in a state-of-the-art facility. Students are also given an introduction to both art history and speech.
• P.E. and Athletics: St. Matthew’s physical education program provides sequential and developmentally appropriate activities designed to provide the students with the skills and knowledge necessary to gain an appreciation for the benefits of maintaining an active and healthy lifestyle. Students receive instruction and practice in basic motor skills, rhythms and dance, creative movement, and tumbling; are gradually exposed to increasingly complex physical activities, cooperative games, and sports. With the opening of the Sprague Center, students are able to participate in indoor physical education and interscholastic after school sports activities. A rooftop sports area above the Sprague Center offers an additional physical education, lunch, and recess play area. A large swimming pool is used seasonally for both class instruction and interscholastic competition.
• Class Retreats and Excursions: All students in Grades 5-8 are involved in the school's retreat program at which time students and their teachers venture outdoors to engage in exciting team and spirit-building activities. In addition, sixth, seventh and eighth graders take extended overnight trips to Malibu Creek State Park, Sequoia National Park, and New York/Pennsylvania/Washington D.C., respectively.
• Student Government: Middle school students participate in school government through the Student Action Leadership Team (S.A.L.T.). Representatives in Grades 5-8 are self-nominated and then selected by a faculty committee. Eighth graders are also elected to executive positions through school-wide elections. S.A.L.T. representatives have responsibility for community and school service and spirit-building activities.

All middle school students participate in the school's Blue/White intramural sports program. Seventh and eighth graders may also join interscholastic competitive teams in a variety of sports, such as volleyball, basketball, soccer, softball, tennis, swimming, track and field, and flag football.