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 sub-series contains various items relating to the Shooting team at Oakham School.

A menu for the Oakham School Rifle Club's Ashburton Celebration dinner on 6 December 1975.

A memorandum from Alan Grieve to Roger Blackmore confirming the arrangements for the OO Dinner.

A letter from Roger Blackmore to Alan Grieve responding to the memorandum AB/26/13/21 and giving feedback from an OO Committee meeting regarding the Dinner on 24 November.

A letter from Roger Blackmore to Alan Grieve regarding a card to be sent to all Old Oakhamians and the catering arrangement for the OO Dinner.

A letter from the Headmaster Graham Smallbone to O.O. Corinna Pike regarding the frescoes in Old School and the forthcoming Old Oakhamian Dinner.

A letter from Alan Grieve to Roger Blackmore commenting on a dinner, probably part of the Quatercentenary celebrations. Two pages A and B.

Old Oakhamian Calendar, published in 1924. Cover with contents: Editorial; List of Addresses of Members of the Old Oakhamian Club - 1924; Meeting of Old Oakhamian Club; Old Oakhamian Luncheon; A Letter from the Headmaster; Cambridge Letter; Officers' Training Corps; A Weekend in Africa; Births, Deaths and Marriages; Old Oakhamian Matches; School Staff - September 1924. Nine double-pages A to I.

The Old Oakhamian Magazine, published in 1933. Contents: Annual Dinner; Cricket and Football; The Golfing Society; The School, 1932-1933; Births, Deaths and Marriages; O.O. Notes; Notices; Football Fixtures, 1933-34. Two double-pages A and B.