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A headmaster's annual report for the academic year 1980-1981. Contents: Registrations/Entry; The Upper and Middle School Houses; Jerwoods; Discipline; Staff; General Academic; The Departments; A-Level and O-Level; University Entrance; The Library; Drama; P.E. and Sport; Sports Centre; Chapel; Voluntary Service; C.C.F.; Duke of Edinburgh Award Scheme; Exploration Society; Sea Scouts and Guides; Senior Societies and Middle School Societies; Careers; Publicity and Local Relations; Audio-Visual Aids Centre; The Oakhamian; The Ashburton Hall; School Council; Sanatorium; Old Oakhamian Club; Oakham School Nursery; Postscript. Seventeen pages A to Q.

A headmaster's annual report for the academic year 1981-1982. Contents: Registrations/Entry/Numbers; The Upper and Middle School Houses; Jerwoods; Discipline and The Decem; Staff; General Academic; The Departments; A-Level and O-Level; Scholarships; University Entrance; Careers; The Library; Drama; P.E. and Sport; Sports Centre; Chapel and the Chaplaincy; Afternoon Activities; Voluntary Service; C.C.F.; Duke of Edinburgh Award Scheme; Exploration Society; Scouts and Guides; Senior Societies and Middle School Societies; Publicity and Local Relations; Audio-Visual Aids Centre; The Ashburton Hall;
The School Council; The Oakhamian; Sanatorium; Old Oakhamian Club; Oakham School Nursery; Postscript. Attached are A-Level results (appendix A), O-Level and A-Level results (appendix B), University Entrance (appendix D). Nineteen pages A to S.

A headmaster's annual report for the academic year 1982-1983. Contents: Registrations/Entry/Numbers; The Houses; The Decem/Discipline; Staff; General Academic; The Academic Departments; Music; Art and Design; Drama; P.E. and Sport; C.C.F. and Duke of Edinburgh Award Scheme; Community Services; Afternoon Activities; Careers; Chaplaincy; The Ashburton Hall; Library; The Oakhamian; The School Council; Oakham School Nursery; Sanatorium; A.V.A. Centre; Postscript. Attached are A-Level results (appendix A), O-Level and A-Level results (appendix B), University Entrance (appendix C), a report to the Headmaster - Computing Department (appendix D). Thirteen pages A to M.

A headmaster's annual report for the academic year 1983-1984. Contents: Numbers and Recruitment; Discipline and Morale; Staff; Academic; Art/Design/Music/Drama; P.E./Sports/Games/Service/Activities; Chapel; Food/Health; Careers/A.V.A.; Oakhamian/School Council; Publicity and P.R.; 1984 and All That. Attached are A-Level results (appendix A), O-Level results (appendix B), Academic Scholarships and Exhibitions (appendix C). Nine pages A to I.

A headmaster's annual report for the academic year 1984-1985. Contents: Some Thoughts on 1984/1985; Registrations/Entry Numbers; The Houses; Oakham Nursery School; Staff; General Academic; Examination Administration; University Entrance; Afternoon Activities; Sport Centre; Chapel; Food; Sanatorium; A.V.A. Centre; Careers Advice/ISCO Tests; Preparatory Schools Liaison/13+ Entry; Publicity/OSEL/Prospectus etc: The Queen Elizabeth Theatre; New Zealand Tour/Kenya Expedition; School Library; Old Oakhamian Club; House Names; Housemasters/Housemistresses; Conclusion. Attached are replies to a questionnaire for prospective parents (appendix A), some additional comments by Michael Stevens, a questionnaire for prospective parents, Overseas Universities Entries (appendix B), A-Level results (appendix C), O-Level results (appendix D), University entrance (Appendix F), a summary on Fastnet. Twenty-Seven pages A to AA.

A headmaster's annual report for the academic year 1985-1986. Contents: The School Year; Second Master's Report; Registrar's Report; Registrations/Entry Numbers; Director of Studies' Report; Scholarship Report; Christopher Dixon Prize; University Entries; A- and O-Level results; The Departments; Prep Schools Liaison Report; The Houses; Examination Administration; Drama and the Theatre; Careers; The Chaplaincy; A.V.A. Centre; Ashburton Hall; The Sanatorium; Library; The School Council; The Oakhamian; Old Oakhamian Club; Nursery School; Playing Fields; The Sports Centre; Afternoon Activities and Societies; Exploration Society; The Teaching Staff; OSEL/Public relations/Appeals; Conclusion. Attached are A-Level results (appendix C), O-Level results, Scholarship Awards (appendix A), Bursaries, University Entries (appendix B). Thirty pages A to AD.

A headmaster's annual report for the academic year 1970-1971. Contents: Numbers; Staff; Academic; Faculty Reports; Chapel; Library; Drama; C.C.F., Scouts, Duke of Edinburgh Award Scheme; Health; Accommodation; School Shop; Old Oakhamians; Second Development Campaign; School House; General. Attached is the Chaplaincy report (appendix A). Nine pages A to I.

A group of four articles entitled the 'New light on Oakham History' by W.L. Sargant which were printed in a newspaper. The articles are based on research undertaken by Mr Sargant in the Muniment Room of Westminster Abbey and written whilst he lived in Sidmouth, therefore in the late 1940s-early 1950s. Four pages A to D.

This focusses on photographs of the Headmaster, Walter Lee Sargant, as well as various photographs of Oakham town in the early 20th century.

A photograph of Father Douglass visiting the School in 1928. The photograph shows Father Douglass, Rev Scriven, Rev Edward Vere Hodge, Rev Frank Jerwood, Helen Hodge and Walter Lee Sargant in front of the Chapel.