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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 sub-series relates to the history of Old School, oldest building of Oakham School, in Cutts Close park. It is made of a collection of photographs and art work; of newspaper cuttings and letters, mostly relating to the debate concerning the refurbishment of the building and preserving the frescoes painted by Mary Sargant Florence.

This series focusses on recreational events for staff by the Common Room and by Oakham School Enterprise Ltd, such as Christmas Parties, Burns Night and swimming pool sessions, from 2005.

This sub-series contains letters concerning Deanscroft house and pupils.

This sub-series focuses on the administration of Clipsham House.

This sub-series focuses on the everyday running of Lincoln House. It contains reviews of the terms and the girls' achievements, as well as house lists an address lists.

This sub-series contains letters related to School House. The items relate to the 2004 naming ceremony of rooms in School House.