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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.

An almost complete collection of the School's magazines dating from 1884.

The Oakhamian Magazine and Old Oakhamian Magazine, recording the Summer term 2015. Contents: News; Features; Academic; Cover Story; Performing Arts; Jerwoods; Trips and Tours; Pastoral; Community Activities; Sport; Staff News; Beyond Oakham; Old Oakhamian; Foundation.

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.

A complete collection of bound books, gathering Oakham School Magazines copies, from 1884 to 2014. Some books may contain issues of the Magazine that would be otherwise missing in the collection.

The Oakhamian Magazine, recording the Spring and Summer terms 1979. Contents: Editorial; School News; Valedictions; Opinion; Excursions and Adventures; Clubs and Societies; Drama; Music; Sport; The School Council.

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.