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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.

This sub-series contains photographs of various Duke of Edinburgh expeditions, since the 1980s.

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

A collection of photographs of the Computer Block since its construction in 1982. The building was built as part of the Quatercentenary Development Plan and was officially opened on 11 July 1984 by Lord Kings Norton.

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 documents, chiefly photographs, of Wharflands, purchased by the then Headmaster Walter Lee Sargant in 1920. The property was converted into a boys’ boarding house for twenty-six boys, while the Old Stables were used for other school purposes. Extension work began in 1928, adding four new dormitories and a large dining hall. The O.T.C. established its headquarters in the new extension. With the boys now living in the extension, the Housemaster and his family could occupied the old house. The first floor was converted into some classrooms, for the teaching of Science and Maths. In 1960 and 1977, a series of improvement and refurbishment work started and changing rooms were modernised, while new rooms were added.

A collection of documents, mainly photographs, of Jerwoods, the Lower School Campus. In 1962 the School purchased the old vicarage on Burley Road, named Peterborough House. In 1967, the Junior boys moved into their new boarding house. In 1974, new houses were erected around Peterborough House. The duo-decagonal Lincoln House for boarding girls was designed by Tom E. Wilson and built by George Duxbury and Sons, the architect and contractors of Round House. Behind it was built the Coleman Building, named after Leslie Coleman, into which Sargants (Day boys) and Ancaster (Day girls) moved in 1975. On 14 May 1974, John Jerwood unveiled the foundation stone and the Junior School was officially opened on 23 November. The houses comprised small dormitories with bunk beds, common rooms, a junior library and playing areas. The Coleman Building was linked to Lincoln House and Peterborough House.

A collection of photographs and art work of School House, and plans of the building.

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.