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This series focusses on the headmastership of Walter Lee Sargant (1902-1929) and contains items relating to the life at School in the early 20th century, its staff and pupils.

Information sheet detailing the new timings of the Form 5 week, due to Covid restrictions, for the Winter term 2020. The item was pinned on the year group's notice board in house.

This series focusses on the headmastership of Oliver Richard Sylvester Bull (1977-1984) and contains items relating to the life at School in the 1970s and 1980s, its staff and pupils. One of the files relates to Michael Stevens as Acting Headmaster for two terms in 1985.

Notices compiled at the end of the Winter term 2018 and sent to Parents. Contents: Director of Operation's Notices; Registrar's Notices; Medical Centre; Music Dates; Oakham Choral Society; Term Dates; Art Calendar; School Archives; Art; Staff Changes. Two pages A and B.

Notices compiled at the end of the Winter term 2017 and sent to Parents. Contents: Change of status requests; Form 3 Registrations; Siblings enquiring for Form 6 entry; Non EEA pupils; Medical Centre; Music Dates; Oakham Choral Society; Term Dates; Art Calendar; Parent Portal; School Archives; Art; Staff Changes. Two pages A and B.

Notices compiled at the end of the Summer term 2018 and sent to Parents. Contents: Change of status requests; Form 3 Registrations; Siblings enquiring for Form 6 entry; Non EEA pupils; Medical Centre; Music Dates; Oakham Choral Society; Term Dates; Art Calendar; School News; Parent Portal; School Archives; Art; Trustee Changes; Staff Changes. Three pages A to C.

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 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 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 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.