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

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 focusses on the Merton building, erected on the site of the old Ashburton Dining Hall. It was in use on the first day of the 1991 Winter term and the official opening ceremony took place on 26 November. Michael McCrum, former Trustee and Master of Corpus Christi, Cambridge, opened the new block. It comprised “spacious corridors, staff rooms for each subjects and twenty-four comfortable and acoustically effective classrooms”. The building was named after OO Thomas Merton (‘32). The Headmaster, Graham Smallbone, planted a tree outside the entrance to commemorate the 450th anniversary of the Diocese of Peterborough. This new building houses the English, Maths and History Departments.

This sub-series is made of items relating to the new Johnsons building, Faculty of Social Sciences, opened on 09 September 2017.

A collection of photographs and architectural plans of the Music School since its opening in 1984.

A collection of photographs of the School theatres, the Barraclough Hall and the QET.

This sub-series is related to the activities of the Oakham School Charities Association. The various files contains photographs of events, programmes and posters advertising those events, reports and detailed accounts of money raised to support charities.

This sub-series is related to the organisation of the Rutland Water Walk for charity. Items include correspondence, map and route details, safety rules and guidance for pupils and staff.

This sub-series contains items related to Oakham School's work with various charities and the local community.

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.