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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.

A box of ephmera from Buchanan's House.

This sub-series is made of various informal photographs of the boys in Deanscroft, especially in the 1960s. It also contains items related to the 50 years Anniversary celebration of Deanscroft & Haywoods House, including a tie designed for the special occasion.

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

A series of photos of frescos in Shakespeare Centre by Mary Sargant Florence (including some images of Old School before it was the Shakespeare Centre). Also included is a letter from Margaret Camester which attaches extract of book to be published about the women's peace movement of 1915 (which contains a pamphlet by Mary Sargant Florence called 'Militarism versus feminism' and biography of her). At the back is a sheet which includes the inscribed stone over the old school door and a translation of it.

This sub-series focuses on the history of the 1993 Organ in the School Chapel. After the 1930 organ expired and was replaced by a computer organ in the 1980s, the headmaster Graham Smallbone commissioned for a new organ to be built. Some items highlight the various proposals, the correspondence focuses on the building and installation of the organ and the photographic file finally shows the organ in Chapel.

This sub-series relates to the history of the Cadets at Oakham School since 1910. The bulk of the collection is made of photographs of inspection throughout the 20th century.

This sub-series focuses on photographs of the Day Boys in Hodge Wing in the 1950s and 1960s.

This sub-series focuses on photographs of girls in Orchard Close and Buchanans House, mostly in the 1990s and early 2000s. It also contains photographs of the Sixth Form cohort.

This sub-series focusses on photographs of Oakham School 1st Shooting VIII, mostly during the 1950s and 1960s, as well as teams competing in the Ashburton Competition at Bisley.