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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.

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

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 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.

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

The items in this sub-series are guidelines and resources related to mental health and wellbeing. Most are documents sent internally and externally to staff, parents and guardians.

The items are related to Medical CAre but do not fit in any other sub-series, based on their topics.

A collection of documents relating to Round House, the first purpose-built girls’ boarding house, built in 1972 on what was School House tennis court. The Architect, Tom E. Wilson, designed a building in the shape of a Dovecote, or a Birdcage. The builders were George Duxbury (OO, '34) and Sons. The new house contained thirty bed-sitters on three floors, built around a central spiral stairway. A common room linked the new building with the War Memorial Library. At the back of the Library were built a small flat and domestic offices. Sixty girls moved in from the beginning of the 1972 Winter term and the boarding house was officially opened on 28 October 1972 by Mrs Haywood.

This collection of documents has been filed by Jane Matthews, Senior Mistress of Oakham School. They related to H.M.C. Co-Educational Group Meetings of Senior Mistresses, resources for staff and pupils regarding wellbeing, maternity leave, health, and various correspondence. The collection spreads over a few years from the late 1980s to the mid-1990s.

The sub-series contains a digital version of John Buchanan's "Operation Oakham" and a list of contents.