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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.

Notes from John Barber to Michael Stevens regarding the celebrations of the 450th anniversary of the birth of Archdeacon Robert Johnson.

A letter from the Headmaster Graham Smallbone to Bryan Waites at the Rutland County Museum regarding celebrating the 450th anniversary of the birth of Archdeacon Robert Johnson and an article in This England.