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This collection covers the history of all the libraries of Oakham School as well as the creation and daily working of the archives.

The Library series has material relating to each regeneration of the library (Smallbone, War Memorial). There is a rich photographic record of the opening and daily running of the Smallbone Library accompanied by administrative documents such as catalogues.

Under the Archives series, material cover correspondence with external readers and research into the history of the school and its pupils. There are also archive committee meeting minutes which show the evolution of the archives from its inception in 2010.

A headmaster's annual report fro the year 1981-1982, including numbers, Academic, Careers, A.V.A. Centre, Library, Art & Design, Music, Physical Education, Sports Hall, Playing Fields, Shooting, Drama, C.C.F., The Duke of Edinburgh's Award Scheme, Exploration Society, Scouts & Guides, Discipline and the Decem, Houses, Chaplaincy, Ashburton Hall, School Council, The Oakhamian, Senior and Middle School Societies, Voluntary Services, Sanatorium, Oakham School Nursery, Old Oakhamian Club; with appendix: A-Level results and leavers' destinations

A letter from the Bursar Tom Reay to Nigel Webb, Second Master, regarding renewing the licences to perform in Old School.

A letter (A) from Marion Hall to Nigel Webb, Second Master, thanking him for a visit to the School and enclosing a short piece (B-D) on Mary Sargant Florence. Four pages.

A note from the Headmaster Graham Smallbone to staff regarding the Thanksgiving service for Henrietta Lea

A letter to the housemasters and heads of schools about the poor behaviour of pupils in the town smoking and general lack of respect in cafes and by hotels.

Notes from the Haileybury Meeting P.E. and Games held at Brentwood School in March 1989, including thoughts on facilities and the teaching of P.E. lessons in the timetable. Three pages numbered A to C.

A fixture card for the school cricket club including 1st, 2nd, 3rd, Senior Colts, Vairous Colts teams and Jerwood teams.