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A collection of photographs and art work of the Barraclough Dining Hall. It was opened on 28 September 1987 by Lord Forte. It contained two dining halls on the ground floor and a staff dining hall, bar and common room above. It was named Barraclough Hall, in memory of Norman Barraclough (OO, 1883) and his widow, Mrs Barraclough, a great benefactor to the school.

This sub-series focuses on Chapel Close, including the Reception building and the School's main entrance through Market Place and the Buttercross.

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 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 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.

This sub-series is made of items relating to the new Johnsons building, Faculty of Social Sciences, opened on 09 September 2017.

A collection of photographs and art work of Old School, oldest building of Oakham School, in Cutts Close park.

A collection of documents, mostly photographs, relating to the Schanschieffs site.
In 1994, the School purchased the Catmose Vale site, behind Rushebrookes house. The original buildings were built in 1836-1837 by William J. Donthorn. They used to be the town’s workhouse, which later became the Catmose Vale Hospital. On the site was built a car park, two Day boys’ houses and the original buildings were converted into two Day girls’ houses. The four houses were officially opened on 17 September 1997 and were named after Rutland villages: Gunthorpe and Hambleton (Day girls), and Barrow and Clipsham (Day boys). The site was named after O.O. Simon Schanschieff ('57), Chairman of the Trustees.

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 of the School theatres, the Barraclough Hall and the QET.