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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.

This collection focuses on the staff who have worked for Oakham School over the years. Material focuses on not only training and teaching, but staff wellbeing, pay and benefits.

There are two series which focus on notable members of staff from the school's history: Jon Wills and Brian Welford. Material for these staff members have been collected by themselves and other members of staff.

Recruitment series includes jobs descriptions for various positions, both teaching and support staff, in the school.

There is a strong collection of policies an guidance for teachers in completing the many administrative and teaching jobs expected.

The Oakhamian Magazine, recording the Winter term 1978. Contents: Editorial; School News; VOIR; Drama; Rutland Weekend Television Presents; Music; Clubs and Societies; Sport; The School Council.

A bound copy of several Oakhamian Magazines from Summer 1993 to Summer 1997.

A bound copy of several Oakhamian Magazines from Spring 1984 to Summer 1987.

The Oakhamian Magazine, recording the Summer and Autumn terms 1981. Contents: Editorial; School News; Talbot Griffith; Religion; Prize winning Letter; Letters to the Editors; Profiles; Features; French Folies; Creative Writing; The Four Elements; Art & Design; Music; Drama; Societies; Ventures at Home & Abroad; Sport; University & Careers List.

This series focusses on photographs of teaching and support staff throughout the years. The bulk of the collection is individual photographs of staff from the 1990s.

The Oakhamian Magazine, recording the Winter term 1976. Contents: New Headmaster Appointed; Editorial; School News; O.O. News; Correspondence; Opinion; Drama; Music; Societies; Miscellany; Sport; C.C.F.; University/Careers List.

The Oakhamian Magazine, recording the Winter term 1977. Contents: Editorial; School News; Clubs and Societies; Drama; Music; Musing-Impressions-Travellers' Tales; Icelandic Summer; Japan; Summer retrospect; Sport; C.C.F.; School Council.

The Oakhamian Magazine, recording the Summer terms 1980. Contents: Editorial; School News; T.C.S.H.; Chapel Notes; Profiles; Correspondence; Creative Writing; Expeditions and Adventures; Art and Design; Music; Drama; Societies; C.C.F. and Duke of Edinburgh Award Activities; Sport; School Officials.