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Stretching back to the headmastership of Dr. Doncaster, this collection comprehensively covers the correspondence, publications, photographs and other ephemera of the headmasters of Oakham School up to the present day. For many of the headmasters, correspondence and rolls calls are a significant theme in their series.

This collection also contains an excellent record of speeches and sermons given by G. Talbot Griffiths and John Buchanan.

The final series on reports covers the headmaster's, deputy headmaster's and registers writings on the state of the school, including topics such as building and estate development, admissions, the curriculum, examination results, and Old Oakhamians.

A note from the Headmaster Tony Little regarding the history of the school, its location, academic performance and co-curricular activities, sports, and school life.

A brochure (A) on Welland Valley prep School, which was never created but was endorsed by Oakham School in Autumn 1999. Enclosing a note from the Headmaster Tony Little (B).

This series focusses on the headmastership of Dr Joe Spence (2002-2009) and contains items relating to the life at School in the 2000s, its staff and pupils.

Minutes of a Parent/Teacher Committee meeting held on 17 November 2001 in the Bowes Room (A). Contents: Apologies; Matters arising from the Minutes; Afternoon Activities; Oakham School Foundation; Security; Inspection; Term Dates; Timings of Parent/Teacher Meetings; Correspondence; Any Other Business; Representatives for Spring term 2002; Date of the next meeting. Enclosing a letter regarding road safety on Kilburn Road (B).

This file focusses on various publications, internal and external, under Tony Little's headmastership.

A letter from the Headmaster Tony Little to Nigel Richardson, Headmaster of the Perse School, regarding the Golden Jubilee and sending photographs of the Queen's visit in 1984.

A letter from the Headmaster Tony Little to Rosemary Goddard regarding visiting the School and the war memorial.

A staff handbook for the academic year 1996-1997. Twelve pages A to L.

This file focusses on matters of the Parent/Teacher Committee during the headmastership of Tony Little.