The Delaware County Intermediate Unit IU25 provides the district with a wide variety of services like specialized education for disabled students and hearing, speech and visual disability services and professional development for staff and faculty.

In 1953, the United States Supreme Court rendered its decision in the case Brown v. Board of Education of Topeka declaring state laws establishing separate schools for black and white students to be unconstitutional.

In April 1964, almost nightly protests against the Chester School Board policy were marked by violence and police brutality.

George Raymond, president of the NAACP Chester branch presented the school board with a list of 10 demands including teacher transfers, transportation of students to schools in other neighborhoods, hiring blacks for supervisory positions and hiring more black secretaries.

[11] Over six hundred people were arrested over a two-month period of civil rights rallies, marches, pickets, boycotts and sit-ins.

A for-profit company, Edison Schools, was hired to try to improve the struggling district's test scores in 2001.

72% of district students are eligible for free or reduced-price lunches, as compared to the state average of 33%.

[21] The Chester Upland School District offers a wide variety of clubs, activities and an extensive, publicly funded sports program.