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The items in this sub-series are related to anti-bullying policies at Oakham School, aimed both at staff and pupils.

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.

This sub-series relates to the success of Oakham School Shooting VIII at Bisley in 1987, including in particular press cuttings.

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 collection of documents, mostly photographs, relating to the Chinses garden and heron sculpture in front of the Barraclough.

A collection of documents, mostly photographs, of Buchanans house, formerly Orchard Close from the 1980s and 1990s.
Orchard Close had been built in 1929 by W.L. Sargant as a private residence along the cricket fields when he retired. Later, in July 1975 the Trustees acquired the house from the school doctor, Dr T.D. Brentnall. In early October 1975, Orchard Close had become a girls’ boarding house. The house was later modernised to accommodate Sixth and Seventh Form girls. It was renamed Buchanans House in Summer 1977, following the retirement of Headmaster J.D. Buchanan. Work was completed on Buchanans house in 1982. The extension was ready for occupation in January 1983 and was officially opened on 23 February by former Headmaster John Buchanan.

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

A collection of documents, including photographs and art works, of Chapmans, formerly Junior House, built in 1910. The Georgian-style house stood on a ground of one-and-a-half acres. It consisted of dormitories and classrooms facing south which were “well-lighted and ventilated”. The Junior House had been built initially in order to provide a well-equipped Junior Department for a limited number of boarders. In 1936, a new wing was added to the house, comprising a large dining hall, a leisure room, and a new sick room. Rooms were also designed for a House Tutor. The original house was improved, especially the kitchens where “all wash-basins were fitted with hot and cold water, and baths and lavatories were added”.
In September 1960, the Junior House was set to become a Senior House and was renamed Chapmans, after Frank Emerson Chapman, first Housemaster of the Junior House. In 1961, a wide new wing was built on what was the playground. The boys could now enjoy the comfort of new changing rooms, a common room and studies. Above, a dormitory accommodation and rooms for the House Tutor were also added. The old dining room was expanded into a former common room.

This sub-series contains Chris Frame's shooting badges and Ashburton medal, won at Bisley in 1966.