Headmasters
The following lists present the Principals of Jamaica College during its entire history.
- Drax Free School, Jamaica Free School and Jamaica High School (1789–1885)
- Rev. G. Ledwich (1810–1815)
- Rev. L. Bowerbank (1816–1818)
- Rev. Urquhart Gillespie Rose (1818–1825)
- Rev. Geo Watson Askew, B.A. (1826–1828)
- Rev. T. H. Gegg, A.M. (1829– ?)
- Rev. O. Handford, M.A. (? –1855)
- Rev. Morrison Myers (1855–1861)
- Rev. John Leslie Main, B.A. (1862–1883)
- Archdeacon William Simms (1883–1885)
- Jamaica College (1885 onwards)
- Archdeacon William Simms (1885–1915)
- Mr. William S. Cowper (1916–1933)
- Mr. Reginald Myrie Murray†, Rhodes Scholar (1933–1941)
- Mr. Joseph W. S. Hardie (son of Bishop William G. Hardie) (1941–1945)
- Mr. Hugo Carl Winston Chambers† (1945–1960)
- Mr. Vincent H. Ennever† (1960–1964)
- Mr. William H. Middleton (1965–1970)
- Mr. Ruel L. Taylor (1971–1993)
- Mr. Lloyd Bryan (1993–1995)
- Mr. Tim Akpeti (acting) (1995–1996)
- Mr. Stuart Reeves (1997–2006)
- Mr. Ruel B. Reid (since 2006)
† indicates principals who attended Jamaica College
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