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A headmaster's annual report for the academic year 1974-1975. Contents: Numbers; Staff; Academic; Faculty Reports; Chapel; Library; Drama; C.C.F., Scouts, Duke of Edinburgh Award Scheme; Health; The School Council; Old Oakhamians; The Oakham School Nursery Group; The International Club; Accommodation; General. Attached is a job description for a Public Relations Co-Ordinator and Conference Organiser (appendix A). Seven pages A to G.

Two letters between the Headmaster Tony Little and O.O. Dennis Peacock regarding websites and an article published in 'Resident Abroad' in 1999.

This series focusses on the headmastership of Tony Little (1996-2002) and contains items relating to the life at School in the 1990s and early 2000s, its staff and pupils.

A letter from the Headmaster Tony Little to Dennis Peacock regarding the Oakham School website.

A letter from the Headmaster Nigel Lashbrook to Parents at the end of the Winter term 2018. Contents: Parent/Teacher Committee; Teaching & Learning; Website and School Portals; Sustainability.

A letter from the Headmaster Graham Smallbone to Parents regarding a review of the Spring term 1986. Contents: Oxbridge Results; Summer Exeat and Parent/Teacher evening for Fourth Form; The Tutorial System; School House; School Uniform; Car Parking; OSCA; Remedial Teaching; School video, Parents' leaflet etc; Telex; Smoking.

A brochure (A) on Welland Valley prep School, which was never created but was endorsed by Oakham School in Autumn 1999. Enclosing a note from the Headmaster Tony Little (B).

This file related to Registrar's annual reports, submitted to the Headmaster and Trustees. The file dates from the headmastership of Graham Smallbone.

This file focusses on various publications, internal and external, under Tony Little's headmastership.