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

This photographic series focuses on the history of the chapel since the laying of the foundation stone. It documents its building and opening, services held in the Chapel and objects used in everyday services.

A small blue Book of Common Prayer stamped Oakham School Chapel Council, with the stamp in the front crossed out and signed 'This is no longer O.S.C.C,. property J.E.O.Lawson Head Sacristan', presented by David Clarkson (O.O. 1964)

A letter from Paul to Joe, thanking him for giving him a special time at Oakham and the dinner party.

This series is related to the buildings on the School campus and documents their history. Most of the collection is made of photographs and artwork, as well as architectural plans. Each sub-series focusses on a different building.

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.

A letter from Paul Spicer to Joe an Angela Spence regarding his visit to the school and the rededication service.

This file focusses on obituaries and tributes written in memory of former Headmaster, Richard Bull.