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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 Grosvenor Talbot Griffith (1935-1958) and contains items relating to the life at School in the mid-20th century, its staff and pupils.

Extract from a 1940 prospectus, published in the Old Oakhamian Magazine. Content: Size; Staff; Fees; Curriculum; Timetable; Diet & Tuck boxes; Games; Activities outside the classroom; Day Boys. Three pages A to C.

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

This sub-series focuses on the dedication of the Second World War memorial in the School Chapel in 1946.

A collection of documents, including photographs and commemorative plaques, relating to the School's cricket pavilions on Doncaster Close since the 19th century.

A list of improvements to the School premises in the 1930s, compiled by Headmaster G. Talbot Griffith for Old Oakhamians. Enclosed are photographs of buildings. Five pages A to E.

A letter from the Headmaster, John Buchanan, to Old Oakhamians regarding the upcoming reunion for the Talbot Griffith generation on 16 July 1972.

A letter from Headmaster G. Talbot Griffith to Old Oakhamians inviting them to lunch and tea on the occasion of the Old Oakhamian Quinquennial gathering on 29 July 1939.

A letter from Headmaster G. Talbot Griffith to Mr Atter regarding his son's possible entry in May, houses' full capacity and fees in 1943.