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 letter from James Lewis sending the medals of O.B. Trooper Scott, including the Natal 1906 medal

Copy of a page from "The Stag" with a letter from C.F.S[cott]

A letter from Bertie Bowes to Malcolm regarding the history of Oakham School O.T.C. cap badge. Items A and B

A letter and booklet on the Humf Letters. The letter is to Dr. Spence from Colin Edgar about the project. The booklet contains information about D. H. W. Humphrey's life and the letters that he wrote to Betty Dawes.