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 file focusses on photographs and art work of Nigel Lashbrook, during his Headmastership (2009-2019).

A group of negatives (A), index (B) and photographs (C to P) of the presentation of the Headmaster's portrait in 2002.

This file focusses on various publication, mostly newspaper cuttings, related to the frescoes in Old School and the painter Mary Sargant Florence and post-medieval mural painting. This file is from the year 1993.

A report on the murals in Old School (Shakespeare Centre) from Bond & Read, Chartered Architects. Contents: Description and History; Appendix; Key Drawings. Seven pages A to G.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2018 and Spring term 2019. Contents: Farewell to Headmaster Nigel Lashbrook; Academic; Performing Arts; Trips and Tours; Geography Trip to Morocco; Geography Trip to Iceland; Pastoral; Activities; Sport; Staff News; Old Oakhamian.

Two similar photographs (A and B) of the Headmaster Tony Little and painter Binny Matthews at Speech Day 2002.

This file focusses on photographs of Tony Little, during his Headmastership (1996-2002).

A collection of documents relating to Round House, the first purpose-built girls’ boarding house, built in 1972 on what was School House tennis court. The Architect, Tom E. Wilson, designed a building in the shape of a Dovecote, or a Birdcage. The builders were George Duxbury (OO, '34) and Sons. The new house contained thirty bed-sitters on three floors, built around a central spiral stairway. A common room linked the new building with the War Memorial Library. At the back of the Library were built a small flat and domestic offices. Sixty girls moved in from the beginning of the 1972 Winter term and the boarding house was officially opened on 28 October 1972 by Mrs Haywood.

This file focusses on photographs and artwork of John Buchanan, during his Headmastership (1958-1977) and various visits to the School in the 1980s and 1990s.