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This series focusses on the headmastership of Rev William Spicer Wood (1846-1875) and contains items created by the headmaster himself as well as items relating to the life at School in the mid-19th century.

This file relates to reports about the School during Graham Smallbone's headmastership (1985-1996).

A report from Rev John Darrall to be published in the Oakhamian Magazine on the charity events organised during the year 1991-1992, including the Rutland Water Walk, a hunger lunch, concerts, and houses events.

A report from Rev John Darrall to be shared in the School Assembly on the charity events organised during the Spring term 1989.

A report from Rev John Darrall to be published in the Oakhamian Magazine on the charity events organised during the Summer term 1989, including house events, a piano marathon and detailing the money raised for the charities supported by the school.

A report from Rev John Darrall on the charity events organised during the Spring term 1989, including the Valentine Disco, Red Nose Day, concerts, houses events and listing the charities supported by the school.

A report from Rev John Darrall to be published in the Oakhamian Magazine on the charity events organised during the Winter term 1988, including concerts, Drama performances, Non-Uniform Day and various houses events.

An end-of-term summary from Rev John Darrall on the charity events organised during the Winter term 1988.

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.