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.

This sub-series focuses on the administration and everyday running of the Junior House/Chapmans.

This series focuses on Stevens House pupils and staff since its opening in 1989 after the conversion of Deanscroft, a former boys' boarding house. Most of the series is made of photographs, house photographs as well as more informal photographs focussing on house events.

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.

A prospectus promoting studying at Oakham School in 1903, with illustrations. Contents: Brief History; Subjects of Instruction; Boarding Houses; Health; Games; Holidays.