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.

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

This sub-series focuses on the daily and running of Deanscroft. It includes house rules and house duty lists.

This series focuses on the boarding girls in Rushebrookes house. It was named after the first School Headmaster, Robert Rushbrooke. The first girls moved in in the Spring term 1980 but the building was officially open only on 22 November 1980. This series contains items related to the daily life of the girls in school and in house, as well as house photographs, mostly from the 2010s.