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| Chaplain William Wright : Starts the Wynberg Free School on 5 November. |
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| Mr. S. De Kock: Last headmaster; the school closes when Mr. De Kock moves away. |
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| James Rose Innes : first Superintendent-General of the Cape Colony on 11 May. |
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| John MacNaughton : appointed first Headmaster of Wynberg Established School on 1 June. |
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| The Education Commission records the name 'Wynberg Free School'. |
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| As no pupil attendance records of the first Free School exist, 1 July 1841 is accepted as the founding date of Wynberg Boys' Schools. |
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| Official opening by Dr. P. E. Faure. |
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| First class took place in one room at Glebe Cottage at 11 a.m. |
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| School Moves : 'Bryndewyn Cottage', corner of Aliwal and Tennant Roads in January. |
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| First School Library opened. |
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| The last girl pupil leaves the School. |
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| Government decides to relegate school to status of "second class elementary school". |
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| Mr. MacNaughton resigns and is instructed to close on 27 February 1863. |
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| Mr. Frederick Brice is granted permission to change Wynberg to a private school on 2 March. |
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| Wynberg parents form the first Board of Managers and reclaim the school after 9 months. |
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| Mr. Burton Tubb : appointed as new Headmaster. |
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| Rev. Frederick Bullen-Moore : appointed as new Headmaster |
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| A building is purchased from the Higgs estate. |
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| The Education Commission records the name 'Wynberg Interdenominational School'. |
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| Senior school subjects are taught again. |
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| Mr. Quirk : appointed substitute Headmaster as Rev. Moore returns to England on sick leave. |
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| A sharp decline in pupil numbers is recorded. |
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| Rev. Moore returns, but suffers a relapse in health within one month. |
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| Mr. Henry Nixon : appointed as new Headmaster, later to become the first President of the South African Teachers' Association in 1887. |
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| Mr. Nixon's son, Henry J. Nixon Junior, is appointed Headmaster. |
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| Strived to upgrade the school's status to "First Class". |
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| Sir Herbert Baker designs new school buildings. |
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| Edward T. Littlewood becomes Headmaster and opens the new buildings on 1 July. |
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| New school consists of 5 classrooms. |
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| Littlewood expands the grounds through purchases of Estates and from donations. |
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| He chooses the new school colours of navy blue and white, devises the first school badge, and creates the uniform of navy blazer with white braiding and cheesecutter banded with school colours. |
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| A boarding house is added, run by Mrs. Littlewood. |
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| William Alfred Clegg becomes Headmaster. |
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| Prefect system introduced with G. Harold Eddy becoming the first Headboy. |
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| First full Prefect Body formed. |
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| School badge changes to reflect the Coat of Arms of Wynberg Municipality. |
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| First School Magazine published. |
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| 5 classrooms, a lobby and a cloakroom are added to the building. |
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| First School Orchestra established. |
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| The Music and Dramatic Society is founded. |
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| Arnold Lorie becomes first Headmaster of the new Junior School as the senior and junior sections separate. |
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| William E. Bowden appointed as Headmaster. |
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| Complex honouring Wynberg's fallen soldiers of World War II is opened. |
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| A new hostel replaces the old, 'Littlewood House'. |
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| Neville R. Blackbeard becomes Headmaster. |
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| Establishes first Parent Teacher Association - PTA |
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| First Founders' Day instituted. |
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| School moves to its current site on the Hawthornden Estate during the fourth term. |
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| Rowan C. Algie becomes Headmaster. |
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| Academic Roll of Honour instituted. |
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| Media Centre, Workroom, Viewing Room and Computer Room come into being. |
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| First Supera Moras awarded. |
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| Wynberg Old Boys' Union presents the Bill Bowden Memorial Pavilion to the school. |
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| Bruce E. Probyn appointed Headmaster, the first Old Boy to achieve the honour. |
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| Keith C. Richardson appointed Headmaster. |
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