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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.