This sub-file focusses on letters sent by the Headmaster John Buchanan to Richard Walker (Head Boy, 1971) and his father, John Walker.

This file focusses on obituaries and tributes written in memory of former Headmaster, John Buchanan, as well as letters from friends and family.

This series focusses on the headmastership of Oliver Richard Sylvester Bull (1977-1984) and contains items relating to the life at School in the 1970s and 1980s, its staff and pupils. One of the files relates to Michael Stevens as Acting Headmaster for two terms in 1985.

This sub-series focuses on the history of the 1993 Organ in the School Chapel. After the 1930 organ expired and was replaced by a computer organ in the 1980s, the headmaster Graham Smallbone commissioned for a new organ to be built. Some items highlight the various proposals, the correspondence focuses on the building and installation of the organ and the photographic file finally shows the organ in Chapel.

A collection of letters relating to OSEL courses, Activity Holidays and events in the 1980s.

This series focusses on the headmastership of Rev Edward Vere Hodge (1879-1902) and contains items relating to the life at School in the late19th century, its staff and pupils. The series contains some of the earliest photographs of Oakham School's collection.

This series focusses on the headmastership of Rev William Spicer Wood (1846-1875) and contains items created by the headmaster himself as well as items relating to the life at School in the mid-19th century.

The Oakhamian Magazine, recording the Winter term 1975. Contents: School News; Correspondence; Drama; The Chatty Catty Page; Jerwoods; Sport; Avete; Valete.

The Oakhamian Magazine, recording the Spring and Summer terms 1976. Contents: Editorial; School News; The School Council; Correspondence; Opinion; Societies; Music; Drama; The Chatty Catty Page; Jerwoods; Sport; R.A.F.; C.C.F.

The Oakhamian Magazine, recording the Spring term 1938 (published in Summer term 1938). Contents: Editorial; School News; Music Notes; Speech Day; Athletic Sports; O.T.C.; The 17th Foot; Scout Notes; Cricket; O.O. News; Cambridge Letter; Acknowledgements. Ten double-pages A to J.