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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.

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

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.

Recollections, a letter and a photograph related to life at Oakham School during the Second World War.

This sub-series is related to 'Crime Day', a special event where Lower School pupils are invited to activities and puzzle solving to explore the school campus.

This sub-series is related to Oakham School's Voluntary Action and includes invitation, programmes, photographs and publicity on events organised by the pupils as their Service.

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.