[2] Founded in 1922 by James Alexander Veasey, a University of Michigan graduate and lawyer formerly employed by the Dawes Commission,[3] the school is named to honor the first headmistress, Winnifred Shureman, who was of Dutch descent.

Financing was arranged by a group of prominent Tulsa businessmen, including Waite Phillips and William Skelly.

The 81st Street facility has since added the Walter Arts Center (1992), the Outdoor Sports Complex, including the Charles H. Brown Football Field (1995), the Duenner Family Science, Math, and Technology Center (2000), and Mary K. Chapman Primary School (2009).

[2] Holland Hall has been recognized by the Oklahoma State Regents for Higher Education for superior college preparation.

Holland Hall is one of only three Oklahoma educational institutions to belong to the Center for Academic Integrity.

Holland Hall is one of four independent schools to participate in the College Work Readiness Assessment (CWRA) project.

Most of the primary classes (English, math, science, history, foreign language) meet five times per cycle.

The Branch Theatre is named in honor of a former headmaster and has a proscenium-thrust stage with seating for over 1200, and a full suspended fly-gallery.

Arts are emphasized from an early age at Holland Hall, where children in grade school engage in performance based activities.

Disciplines include orchestra, choir, jazz band, modern dance, and visual arts.

[2] Beginning in 2016–17, most teams (except field hockey) began competing in the Oklahoma Secondary School Activities Association.

The boys' soccer team won the 2008 SPC Championship with a 5–3 win over St. Mark's School of Texas.

The boys' soccer team also won the 2009 SPC Championship with a 2–0 win over John Cooper School.

Their rival in the Southwest Preparatory Conference was the St. Mark's School of Texas Lions, which had beaten Holland Hall to win the SPC Division I football championship several times.