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.

This sub-series focuses on photographs of boys in School House since the 1940s.

This file focusses on material relating to Jon Wills' time at Oakham School as a pupil.

This file relates to Jon Wills's time at Oakham School as a pupil and staff.

This series focuses on Round House pupils and staff since its opening in 1972 as the first purpose-built girls' boarding house. Most of the series is made of photographs, house photographs as well as more informal photographs focussing on house events.

This sub-series focuses on photographs of girls, living in Round House since its inception, as well as well Leavers photographs of both School house and Round House pupils since the 2000s.

This sub-series focuses on photographs of girls in Orchard Close and Buchanans House, mostly in the 1990s and early 2000s. It also contains photographs of the Sixth Form cohort.

This series focuses on the boarding girls in Orchard Close (built in 1929), later Buchanans House. It became a girls' boarding house in early October 1975 and Michael Stevens was its first Housemaster. It was renamed Buchanans House in Summer 1977, following the retirement of Headmaster J.D. Buchanan. Work was completed on Buchanans house in 1982 and the extension was ready for occupation in January 1983. The house was first a Seventh Form house and transitioned to a Middle School house in the 1980s.

Magazine named The Oakhamian, stappled; a photograph of boys and girls in uniform walking on the cover; 80 pages; contents: Editorial, School News, Co-Education - Seven Years On, A Guide to A Level Options, Civil Manoeuvres, Societies, The Arts, C.C.F., Duke Of Edinburgh award and Scouting Activities, Sport, The School Council; with photographs of sporting events, plays, DofE Gold Award winners, CCF inspection

Two black and white photographs of the extension to Buchanans.