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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 file focusses on obituaries and tributes written in memory of former Headmaster, Richard Bull.

A photograph of the Headmaster Graham Smallbone conducting the orchestra. Date is unknown.

This file focusses on matters of the Parent/Teacher Committee during the headmastership of Graham Smallbone.

This file focusses on photographs of Tony Little, during his Headmastership (1996-2002).

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.

A letter from the Headmaster Graham Smallbone to T.M. Reay, Mrs Wheway, Roger Blackmore and the Housekeepers, containing the minutes of a meeting regarding OSEL, conferences and support to house staff. Two pages A and B.

A letter (A) from the Headmaster Graham Smallbone to be sent to Old Oakhamians after the Appeal launch. Attached are two lists (B and C) of recipients.

Four sample letters (A to D) from the Headmaster Graham Smallbone to be sent to potential donors to support the 1993 Development Plan.

A letter (A) from Graham Smallbone, Headmaster, and Roger Blackmore, Joint Secretary of the the Old Oakhamian Club, inviting Old Oakhamians to a special reunion. Attached is a reply slip (B).