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A collection of photographs and artworks of the school campus and buildings, and pupils and staff.

There is one series dedicated to a large collection of photographic negatives which show the campus, daily life at school, and special events. These cover the period 1978 - 1988.

One series focus on the frescoes painted by Mary Sargant Florence in Old School and is rich in research about the frescoes and the artist.

A collection of reports and financial statements, and letters, related to the activities of Oakham School Enterprises Ltd (OSEL), spanning from 1978 to 1995.

This sub-file focusses on the registration of Oakham School Enterprises Ltd with the Companies Registration Office, and includes correspondence and legal documents.

A letter listing actions taken as a result of the Report of Peat, Marwick, Mitchell & Co on 27 May 1982. Two pages A and B.

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

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.

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 file focusses on the organisation of various Oakham Art Festivals in the early 1990s.

A list of telephone numbers and extensions in case of emergency for the National Youth Chamber Orchestra stay at Oakham School.

A newssheet from the Headmaster Richard Bull listing the achievements and events of the Summer term 1984, including future term dates.