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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.

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.

A newsletter from the Oakham School Foundation, 'Donum', issue no.1. Contents: 30 years of Co-Education, Three new Scholarships, Parent Fund, Legacies, Annual Giving "Investing in the Future", Old Oakhamian Parents' Society, International Receptions, Class of 2002, Message from the Chairman, From the Headmaster, 10 Year Development Plan, From the Foundation Director.

This series focuses on various dedication and rededication services since the opening of the School Chapel. Most items are orders of services.

Correspondence between HMC Schools regarding the Golden Jubilee in 2002.

Two letters between the Headmaster Tony Little and Rosemary Goddard, sister of Geoffrey Brittlebank who dies in the Second World War, regarding visiting the War Memeorial.

Two letters between the Headmaster Tony Little and Ray Tyler regarding the development of cricket at Oakham School and the position of Cricket co-ordinator in 1999.

Two letters between Michael Yeld and the Headmaster Tony Little regarding the donation of a drawing of College House, made by Robert Norman Yeld when a pupil.

Three letters between Eileen Buxton and the Headmaster Tony Little regarding the death of Robert Henry Buxton, and the donation of his Oakham School crest to the School in 2001.

This file focusses on letters received/sent by the Headmaster Tony Little during his headmastership (1996-2002).