In well over a century the School has seen only seven Headmasters. The steady growth in size of the School and its strong traditions are largely the result of the dedicated service of this small group of scholars and administrators. Their names and years of office are listed below.

 HeadmasterFormer Positions
E I ROBSON (1889-1900)
BA (Cantab), MA (Melbourne)
Formerly Classical Tutor of Ormond College, Melbourne
C H HODGES (1900-1910)
MA (Oxon)
Formerly Headmaster, Townsville Grammar School
W A PURVES (1910-1922)
MA, (Oxon)
Formerly Headmaster, Toowoomba Grammar School
L C ROBSON (1923-1958)
CBE, MC, MA(Oxon), BSc(Sydney)
Formerly Senior Mathematical Master, Geelong Church of England Grammar School
B H TRAVERS (1959-1984)
AM, OBE, MA BLitt(Oxon), BA(Sydney) FACE
Formerly Headmaster, Launceston Church Grammar School
R A I GRANT (1984-2002)
AM, BEc(Sydney), DipEd(University of New England), BEd(Melbourne), MACE
Formerly Deputy Headmaster, Canberra Grammar School
T A WRIGHT (2003- )
PhD, DipEd, BSc(Hons), FACE, MRACI, CChem
Formerly Headmaster, All Saints College Bathurst, 1993-2002 and Second Master Trinity Grammar School, Summer Hill. Dr Wright is a member of AHISA and a member of the NSW Board of Studies.

The portraits of all former Headmasters are to be found in the War Memorial Hall. The present Headmaster joined the School in January 2003.