Kingston High School was established on April 16,1938 as Kingston Senior School, the first of its kind in the island, at a time when Edward Denham was Governor of Jamaica. The school was officially opened on May 4, 1938, by Mayor of Kingston, the late Oswald E Anderson. The first principal was the late Mr. A. J Newman, who had previously served as principal of the Mico Training College, and accommodation was provided for eight hundred (800) learners. Students from age twelve (12) were admitted from Allman Town, Chetolah Park, and Jones Town Primary School. Regular subjects were taught, and practical skills were also emphasized.

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To provide additional secondary spaces, a shift system was introduced. The uniform then was blue tunic with a blue striped band for girls and khaki pants for boys. In later years the colour of the girl's tunic and the boy's shirt changed to gold. 

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In the early 1950s, experimental classes in secondary education were conducted. This was very successful with many students passing their Secondary School Certificate Examinations, obtaining the first and second highest level passes and later entering the university system. Students also sat the Jamaica Local Examinations in the first, second and third year.

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Since its earliest days, the school has gone through many name changes: Senior School, Kingston Junior Secondary, Kingston Secondary, Kingston Comprehensive High School and Kingston High School. Over the years, the school has produced many outstanding scholars who have gone on to proudly serve their country in various endeavors.

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