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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 group of negatives used as the illustrations in "The Story of Oakham School".

A transcript written by John Barber in 1992 of F.C. Doherty's pamphlet published in 1932, titled 'The Story of Oakham Church, School and Castle', price sixpence. A copies are almost unattainable, Mr Barber wrote a copy to be kept permanently in the School Archives. Three pages A to C.