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A letter from the Headmaster Graham Smallbone to Parents regarding a review of the Winter term 1985. Contents: Reports; Scholars; Examinations; Appointments; School accounts; Insurance; Music fees; Activity holidays; Games; Chad '86 Appeal and OSCA. Two pages A and B.

A letter from the Headmaster Tony Little to Parents regarding a review of the Winter term 2001. Contents: Achievements in Music and Drama; Debating; Sports; International Baccalaureate; Staff; Road Safety; E-mail; Next term.

A letter from the Headmaster Tony Little to Parents regarding a review of the Spring term 2001. Contents: Sporting achievements; Debating; Arts, Music and Drama; Mobile Phones; Pubs, Clubs and Alcohol; Match Day Information; Summer term events.

Four pages (A to D) from a 1919 photo album, with captions below the photographs. Contents: Main entrance (School House), pupils after school fire, 1919; 'Tudor House' in Boughton; Rugby 1st XV, 1919; Burleigh gardens and pond; Old Hall and the quad; A cricket match; Lord French inspecting the cadets; St John's College; pupils in the quad; the Long Dormitory boys; a dog; Coates, 1919; pupils at the baths; Burleigh woods and hill; Market Place; F.C. Dwyer; Cricket 1st XI, 1919; The Rectory; C.F. Bayley.

A photo album containing several photographs of the School buildings, including the interior of the Old School, the School House quad, a Physical Laboratory, The School House, School House dining hall and new changing rooms, Doncaster Close, the Gymnasium (now Queen Anne).

This file focusses on letters received/sent by the Headmaster Tony Little during his headmastership (1996-2002).

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 speech given by Headmaster John Buchanan on Speech Day 1965, paying tribute to the new Chairman, Thomas Haywood, discussing three innovations to the education at Oakham School - a small Sixth Form house, the building of a Technology Department, and the establishments of setting by subjects and tutors, and sporting achievements. The speech is typed, with hand-written notations. Six pages A to F.

A speech given by Headmaster John Buchanan on Speech Day 1972, paying tribute to Mr Eric Weiss who opened the new Sports Hall, discussing the Co-Education, sporting achievements and staff news. The speech is typed, with hand-written notations. Twelve pages A to L.

A photograph of a rugby player in the School House quad, probably in the 1990s..