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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 sub-series relates to the history of Old School, oldest building of Oakham School, in Cutts Close park. It is made of a collection of photographs and art work; of newspaper cuttings and letters, mostly relating to the debate concerning the refurbishment of the building and preserving the frescoes painted by Mary Sargant Florence.

A collection of photographs and art work of College House, formerly the Old Vicarage, which was the Sanatorium before becoming the first girls' boarding house in 1971. Also contains a large file on the architecture and history of the building.

A book recording dates and times of services in the School Chapel, including the initials of the officiant, the attendance, the preacher, and the collections from Winter term 1991 to Spring term 2014.

A book recording dates and times of services in the School Chapel, including the initials of the officiant, the attendance, the preacher, and the collections from Spring term 1978 to Summer term 1991.

This sub-series is related to services held in the School Chapel since the laying of the Foundation stone in 1924.

This sub-series focuses on photographs of the School choir over the years.

A photograph of the Oakham School Choir at Greenwich Naval College on 25 June 1998 on the occasion of the last Royal Navy choral evensong at the college.

This series focusses on the headmastership of Graham Smallbone (1985-1996) and contains items relating to the life at School in the 1980s and 1990s, its staff and pupils.

A letter from the Headmaster Graham Smallbone to Parents regarding a review of the Spring term 1986. Contents: Oxbridge Results; Summer Exeat and Parent/Teacher evening for Fourth Form; The Tutorial System; School House; School Uniform; Car Parking; OSCA; Remedial Teaching; School video, Parents' leaflet etc; Telex; Smoking.