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This file relates to the Headmaster's Annual report to the Trustees, from the 1950s to 1980s. The reports cover all aspects of School, academic, examination results, extra-curricular activities, Estates and Maintenance, staff and individual faculty report, vision for the future of the School. All reports are private and confidential.

A bound copy of several Old Oakhamian Magazines from 1985 to 1990.

The Old Oakhamian Magazine, published in September 1989. Contents: Our First Lady President; Annual Dinner; O.O. Day and A.G.M.; Regional Reunions; School News - Round-up; O.S.E.L.; O.S.C.A.; Oakham Festival Week; Music; Drama; C.C.F.; Duke of Edinburgh's Award Scheme; O.S.E.S.; Sport; New Members; Address Changes; Engagements, Marriages, Births & Deaths; Obituaries; O.O. News; Letters; Nostalgia; O.O. Golf Society; O.O. Rifle Club; O.O. Lodge; Club Colours/School Shop; Notices; Diary Dates; Rugby Fixtures.

Two parts of 'Philosophy of Education', included in John Buchanan's book 'Operation Oakham'. A typed draft, with hand-written amendments. Twenty-six pages A to Z.

This series focusses on the headmastership of Graham Smallbone (1985-1996) and contains items relating to the life at School in the 1980s and 1990s, its staff and pupils.

The Old Oakhamian Magazine, published in September 1991. Contents: The Bad News First; John Jerwood; This Year's President; Annual Dinner; O.O. Day and A.G.M.; Regional Reunions; School News Round-up; Staff; OSEL; Academic Results; Sporting Honours; Chapel; OSCA - Appeals Arrive Daily; Music; Drama; C.C.F.; DofE; O.S. Exploration Society; School Sport; When Life was Pretty Tough; Hardships of a Day Boy; Madness and Horror; Letters; New Members; Addresses of Members; Engagements, Marriages, Births & Deaths; Obituaries; O.O. News; O.O. Sport; O.O. Lodge; Club Colours/School Shop; Notices; Diary Dates.

A bound copy of several Oakhamian Magazines from Spring 2009 to Summer 2011.

A bound copy of several Oakhamian Magazines from Winter 2011 to Summer 2014.

This file focusses on letters received/sent by the Headmaster Graham Smallbone during his headmastership (1985-1996).

The Oakhamian Magazine, recording the Spring and Summer terms 1978. Contents: Editorial; School News; Co-Education - Seven Years On; A Guide to A Level Options; Civil Manoeuvres; Societies; The Arts; C.C.F.; Duke Of Edinburgh Award and Scouting Activities; Sport; The School Council.