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This sub-series focuses on photographs of boys, living in Junior House/Chapmans since its inception. The bulk of the collection gathers photographs from the 1950s to 1980s.

This sub-series focusses on various photographs of the pupils and staff of School House as well as various documents related to the history of the house.

This sub-series focuses on various items related to the history of Hodge Wing.

This sub-series focuses on photographs of boys, then girls, living in College House in the 1960s and 1970s.

A collection of documents related to John Barber's book, "The Story of Oakham School". The sub-series includes photographs, letters received by the author, press cuttings advertising the publication and the book.

This photographic sub-series focuses on the Millennium celebration and the objects made for the event.

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

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

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