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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.

A postcard from J.W.G. to G. Talbot Griffith on 25 October in the 1930s. The postcard shows School House and the Buttercross.

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 the Headmaster G. Talbot Griffiths to teaching staff regarding the renaming of the forms in the School from Easter term 1956.

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.

A letter from Headmaster G. Talbot Griffith to Mr J. Taylor regarding his son's entry to the Junior House in 1945.

A letter from Headmaster G. Talbot Griffith to Mr E. Clarke regarding his son, J.G. Clarke, having been accepted by Barclays Bank Limited as a Scholarship candidate and his entry to Oakham School in September 1950.

A letter from former Headmaster, G. Talbot Griffith, to O.O. Alan Jolly regarding gifts presented at a gathering and reminiscences of Alan Jolly's time at Oakham School.