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This series focusses on the headmastership of John David Buchanan (1958-1977) and contains items relating to the life at School in the 1960s and 1970s, its staff and pupils. The bulk of the series consists of books, publications, letters, speeches and sermons written by Mr Buchanan himself.

This file focusses on various speeches given by John Buchannan during his headmastership and later. The bulk of the file is an almost complete collection of his Speech Day speeches.

This series focusses on the headmastership of Graham Smallbone (1985-1996) and contains items relating to the life at School in the 1980s and 1990s, its staff and pupils.

This series focuses on a large range of services held in the School Chapel, such as memorial services, confirmation and baptism services, carol services, weddings, and the weekly and Sunday services attended by pupils. Most of the items are orders of services.

This file focusses on letters received/sent by the Headmaster Graham Smallbone during his headmastership (1985-1996).

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.

A sermon given by John Buchanan at Oakham School on 30 March 1958 and at Uppingham School on 24 May 1959, relating to the concept of truth and Luke 20, 19-26. The sermon is typed, with hand-written notations. Nine pages A to I.

Order of service for a joint service of Thanksgiving for Oakham and Uppingham Schools in Peterborough Cathedral on 18 November 1979 (A). Enclosed is a memorandum on the Peterborough Cathedral Foundation Service (B).

This sub-series contains books used by pupils during services in chapel or books published by staff or Old Oakhamians and given to the school. A large part of this sub-series contains hymns books compiled by Rev T.C.H. Clare ('29).

A photograph of Oakham School girls' hockey team playing in a match against Uppingham.