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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 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.

This file relates to Michael Stevens, Acting Headmaster for two terms in 1985. The bulk of the collection is letter to Parents.

A letter from the Acting Headmaster Michael Stevens to Parents regarding the term's sports achievements, Music concerts, Drama news and the influenza vaccination.

A complete collection of bound books, gathering Old Oakhamian Magazines copies, from 1899 to 2002. 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 1987. Contents: Editorial; School News; Tributes to Retiring Staff; Industry and Oakham School; Some Reviews from "On the Road"; Drama; Music; Art and Design; Societies; Tours; Expeditions; D of E and C.C.F.; Sport.

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

A bound copy of several Oakhamian Magazines from Spring 1972 to Summer 1976.

This series relates to various annual reports presented to the Trustees, including Headmaster's reports, Registrar's reports and Second Master's reports. The series spans over three Headmasters, John Buchanan, Richard Bull and Graham Smallbone.

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.