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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 collection of photographs and other documents relating to the history of the Art and Design buildings. On 25th April 2009, the Jerwood School of Design was officially opened, even though it had been in use since September 2008 by teachers and pupils. It was built on the site of maintenance yard garages, adjacent to the Sports Hall.

A collection of documents, including photographs and commemorative plaques, relating to the School's cricket pavilions on Doncaster Close since the 19th century.

A collection of photographs and art work relating to the whole School Campus, in particular aerial photographs from 1937 of the School and the town, and a file of individual photographs of buildings around the campus. The oldest items in this sub-series date back to the 19th century.

A collection of photographs and art work of College House, formerly the Old Vicarage, which was the Sanatorium before becoming the first girls' boarding house in 1971. Also contains a large file on the architecture and history of the building.

A collection of photographs and architectural plans of the Music School since its opening in 1984.

A collection of photographs of the School theatres, the Barraclough Hall and the QET.

This sub-series relates to Remembrance services held in the Chapel or other churches in Oakham.

This sub-series contains photographs of the exterior and interior the School memorial Chapel throughout the years. The earliest photographs showed the chapel being built in 1924-1925.

This sub-series is related to services held in the School Chapel since the laying of the Foundation stone in 1924.