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 sermon given by Headmaster John Buchanan on Remembrance Sunday 1958. The sermon is typed, with hand-written notations. Seven pages A to G.

A sermon given by Headmaster John Buchanan on Remembrance Sunday 1960. The sermon is typed, with hand-written notations. Seven pages A to G.

A sermon given by Headmaster John Buchanan on Remembrance Sunday 1975. The sermon is typed, with hand-written notations. Nine pages A to I.

A sermon given by Headmaster John Buchanan on Remembrance Sunday on 13 November 1976. The sermon is typed, with hand-written notations. Eleven pages A to K.