Headmasters of Wolmer's Boys' School
- Albert Dews, Esq. 1895-1901
- William Cowper, Esq. 1901-1915
- F.M. Peachell, Esq. 1915-1917
- Rev. William Simms 1917-1919
- Sir Reginald Murray 1920-1933
- Sir Philip Sherlock 1933-1938
- Rev Lewis Davidson 1939-1942
- J.R. Bunting, Esq. 1943-1949
- Dr. Simpson 1950-1953
- Major Norman Jackson 1953-1964
- H.N. Walker, Esq. 1964-1966
- Dr. Donald Bogle 1966-1971
- Richard Morris, Esq. 1971-1978
- Gilbert Smith, Esq. 1978-1979 (acting)
- E.Coleridge Barnett 1979-1998
- Mrs DeAnn Robb 1998-2002 (acting)
- Dave Myrie, Esq. 2002-2008
- Dr Walton Small 2008–present
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