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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.

This collection highlights the work and life of Oakham School pupils both during and after their time at the school. The collection has an excellent representation of the careers, work, and exam aspect of school life, including examination results, leaver destinations, work experience and information on Project 20/20.

There are detailed records on the council, Decem and prefects, particularly in their recruitment, meeting minutes, and handbooks.

In several of the series, there is a strong photographic collection illuminating the rich daily life of the school and its pupils. This is shared alongside copies of pupil magazines, arts calendars, and records of pupil achievements.

A letter From Nigel Webb, Second Master, to the Housemasters and Heads of School regarding the poor behaviour of pupils in the town, smoking and general lack of respect in cafes and around hotels.

Some notes written by Jane Matthews at a Senior Mistresses Conference (Midlands), including the programme of the day and a list of participants.

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.

The Oakhamian Magazine, recording the Summer term 1999. Contents: Editorial; OSCA; Speech Day; Chess; Drama; Music; French Trips; Leavers; Dublin; Duke of Edinburgh Award Scheme; A-Level Art & Design; Geography Expedition to Morocco; Corsica '99; House Reports; Sports; Oakham School 2050.

A bound copy of several Oakhamian Magazines from Winter 1997 to Summer 2000.

A collection of photographs and art work of College House, formerly the Old Vicarage, which was the Sanatorium before becoming the first girls' boarding house in 1971. Also contains a large file on the architecture and history of the building.

This file focusses on artwork of College House, including drawings and a watercolour.

A copy of a drawing of College House and the Chapel in 1968 by John Suraswadi, with a note from John to Patrick from 2009.