Riverside students can also specialize in courses through the Engineering Academy or the Math and Science Magnet Program.

The Early College, Engineering, Math and Science, plus Liberal Arts courses of study are known as the school's four learning communities.

[5][6] Architect Victor Earl Mark (1876–1948) designed Lee High School with William B. Ittner of St. Louis in 1926–27.

The top floor stucco of the four transepts feature a coat of arms, in which a central figure reaches for a star on the left, while a tree occupies the right side.

This made Lee and Jackson the two oldest Jacksonville high schools operating at their original sites.

The band, led by singer Ronnie Van Zant, was renamed Lynyrd Skynyrd after coach Leonard Skinner sent guitarist Gary Rossington to the principal's office for wearing his hair long.

Before that time, the swim teams trained at the Episcopal Church of the Good Shepherd Pool, located about a mile north.

In the summer, it becomes a free public pool operated by the City of Jacksonville Parks & Recreation Department.

In 1991, a new two-floor classroom building was built behind the original structure to accommodate the addition of Ninth Grade.

The educational partnership, funded by the Bill & Melinda Gates Foundation, was designed to raise Lee's graduation rate and improve college readiness, especially among minority and low income students.

Cumber and Lee High School respectively received $500 checks from the affiliated Florida Engineering Foundation (FEF).

The original building's courtyard, roomy stairwells, and ample hallways give students a healthy amount of physical space.

[19] Riverside, and Andrew Jackson are the two oldest Jacksonville high schools still operating at their original sites, with Stanton the oldest overall continuing secondary education institution in Jacksonville, starting as a Freedmen's Bureau-run school in 1868 for Black students.

[22] In April 2021, Amy Donofrio, a Riverside teacher who co-founded a program promoting juvenile justice, EVAC Movement, was asked to take down a Black Lives Matter sign in her classroom.

After complaining that the timing was retaliation for live streaming white members of community meetings making "questionable comments" about the name change, she was administratively reassigned.

[23] The Southern Poverty Law Center has filed a lawsuit against Duval County Public Schools.

After the incorporation of ninth grade in 1991–92, the total number of students slowly rose to a high of 1900 in the 2005-06 year.