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This sub-series focusses on the Ashburton building, formerly the Haywood building.
Colonel Thomas Haywood, Chairman of the Trustees, laid the foundation stone of a new building, which was to bear his name, on 13th June 1964. The architects of this new academic building were F.J. Lenton & Partners. It came to use in September 1965 and was officially opened by Group Captain Douglas Bader. It housed the Geography and Modern Languages Departments. It comprised nine classrooms and the Jerwood Hall in the basement, which was equipped as a lecture hall, cinema and television room. In 1978, a new extension to the Haywood Building saw the addition of six classrooms and ancillary rooms to the Modern Languages, Geography and Audio Visual Aids Departments. The Haywood building on Church Street was extended in 1984. It was renamed 'Ashburton' in 1989 and now houses the Modern Foreign Languages and Classics departments.

A black and white photograph of boys on campus, walking outside the Barraclough Hall and the sun dial, looking towards Ashwell Road, in the 1950s or 1960s. The photograph was taken by Photo-Reportage Ltd and the number of print is stamped on the back: 147847.

A black and white photograph of the south front of the Barraclough Hall, before the construction of the Music School.

A photograph of the Oakham school 1st XI cricket team.

A booklet with a white cover ans spiral bound, on a first estimate for Oakham Innovation Centre. Contents: Comparisson between options, Summary of Estimate, List o drawings and other information, Exclusions, Schedule of Areas, Design Reserve and Contract Contingency, Inflation an Programme, Detailed analysis of construction costs

9 photos of Chapmans house including inside the sitting room of the housemaster, boys bedrooms, showers, dining room and outside playing area. Some writing on reverse of the photos.

A series of permissions letters and negatives relating to the publication of J.L.Barber's The story of Oakham School.

A photograph of boys at cricket practice on Doncaster Close in the 1960s. The photograph was taken by Photo-Reportage Ltd and the number of print is stamped on the back: 862824.

A copy of the newspaper article which includes the picture of the 1914 1st XI Oakham Cricket team and their story.