The Booker T. Washington School, which opened in 1869 at 430 West Adams Avenue[3][4] near Geyer Road was built for African-American students to attend.

In 1896, Kirkwood offered the first four-year high school program in St. Louis County; 10 students were members of the first graduating class in the spring of 1897.

The privately funded Walker Commons enclosed the theater lobby area connecting the Center to the main campus.

[11] In August 2020, the board of education approved the hiring of the Kansas City firm Encompass Resolution, LLC to analyze and make recommendations about the district's climate related to the reporting and handling of sexual abuse allegations.

[13] The lawsuit alleges federal civil rights and Title IX violations and estimates that more than 25 district employees have been involved in sexual harassment, abuse, or discrimination against students over the previous 40 years.

[16] On July 16, 2021, a lawsuit was filed in St. Louis County which alleges that a different former Kirkwood High School teacher and coach sexually abused a student in the 1980s.

The suit alleges that high school administrators failed to "do anything to investigate, reprimand, deter, remedy and/or punish [the employee's] conduct" and that staff started "openly gossiping, joking, and spreading rumors about Plaintiff" once they became aware of the abuse.

[18][19] Their report stated that their analysis found thirty staff members involved in substantiated allegations of sexual misconduct or abuse that extended over more than four decades.

The audit found numerous long-standing deficits in the district's culture and climate related to sexual abuse, misconduct, and reporting.

[20] The program was started by Denver Miller, who coached for forty-three years, earning 790 victories and induction into the Missouri Basketball Hall of Fame.

After the project was delayed because of the removal of water pipes that were deep in the ground, the first home game on the new Fieldturf was played on October 1.

[citation needed] The Kirkwood Pioneers won their second State Championship in 2016 by defeating Blue Springs High School 31-14.

In 2013, the group competed in the National Orchestra Cup at Alice Tully Hall in Lincoln Center and earned third place.