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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 sub-series focuses on the history of the 1993 Organ in the School Chapel. After the 1930 organ expired and was replaced by a computer organ in the 1980s, the headmaster Graham Smallbone commissioned for a new organ to be built. Some items highlight the various proposals, the correspondence focuses on the building and installation of the organ and the photographic file finally shows the organ in Chapel.

A letter from the Headmaster Graham Smallbone to Peter Collins regarding the carvings on the organ and the tuning of the new organ.

A letter from the Headmaster Graham Smallbone to Peter Collins regarding the installation of the organ and the proposed festival for the following year and discussing an exhibition in the Bowes Room.

A letter from Graham Smallbone to Peter Collins regarding problems with the new instruments and the upset at the unfinished nature of the organ.

A letter from the headmaster Graham Smallbone thanking Peter Collins, Organ Builder, for all of his work on the new organ and, despite it's unfinished nature, how magnificent the instrument is.

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).