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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.

A letter from the Headmaster Graham Smallbone to Dermot Gilvary, Head of Drama, regarding some décor being nailed to the woodwork in the Shakespeare Centre and proper use of the building.

A letter from the Headmaster Graham Smallbone to O.O. Henry Blagg regarding the press coverage of the debate concerning the frescoes in Old School and the plan for the restoration of the building.

A letter from the Headmaster Graham Smallbone to David Smith and Ian Robson regarding the refurbishment of Old School and giving consideration to the needs for lighting and curtaining.