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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 photograph of the south front and stairs of the Chapel, possibly taken in the late 1950s-early 1960s. The photograph was taken by Photo-Reportage Ltd and the number of print is stamped on the back: 862849.

This sub-series is related to services held in the School Chapel since the laying of the Foundation stone in 1924.

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

A book for The Order for the Administration of The Lord's Supper or Holy Communion and other rites and ceremonies of the Church according to the use of the Church of England, together with the form or manner of making, ordaining and consecrating of Bishops, Priests and Deacons. This book was given to Oakham School in memory of Rev William Spicer Wood, Headmaster, from his family.

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 photograph of the chancel of the Chapel, showing the altar and the cross, possibly taken in the late 1950s-early 1960s. The photograph was taken by Photo-Reportage Ltd and the number of print is stamped on the back: 157593.