This series is related to the buildings on the School campus and documents their history. Most of the collection is made of photographs and artwork, as well as architectural plans. Each sub-series focusses on a different building.

This series focuses on School House pupils and staff in the 20th century. Most of the series is made of house photographs, various informal photographs as well as records books and punishment books.

A photograph of a dinner at Oakham School in 1963, showing pupils of Hodge Wing and School House in the Dining Room. The photograph was taken by Photo-Reportage Ltd and the print number is stamped at the back: 862873.

Seven photographs taken by Photo-Reportage Ltd, at various dates, in the 1960s. The photographs show pupils in the School House dining room, in their dorms and in the quad.

A photograph of pupils eating in the School House dining room in the 1960s. The photograph was taken by Photo-Reportage Ltd and the print number is stamped at the back: 157562. A number is written in the bottom right corner: 62.