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

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.

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 the Junior House/Chapmans pupils and staff since its opening in 1910. It first comprised the Junior Department with facilities for boys boarders and classrooms. The house was renamed Chapmans in September 1960, after Frank Emerson Chapman, first Housemaster of the Junior House; it became a Senior House. Most of the series is made of photographs, house photographs as well as more informal photographs.

This series focuses on the boarding boys in Deanscroft, since its opening in 1948. The Headmaster himself was Housemaster, until 1971. Deanscroft boarding house was closed on Speech Day 1989, prior to its conversion into Stevens, a boarding house for girls. The boarding boys were moved to the newly built Haywoods House on Kilburn Road. The items include the complete set of house photographs and informal photographs showing boys around the house and on campus, as well as duty records.

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.

The inventory for Junior House. Transfer from E. Pickering Clarke to the Trustees. Contains information on the building, its fixtures and fittings, the dining room, kitchen, garden, toilets, pantry, sick room, matron room, dormitory, study, classroom, bathrooms, coal house, workshop, tool shed, gardens and tennis nets. Items A to AG

Magazine named Oakhamian Magazine - The Magazine of Oakham School and The Old Oakhamian Club; 139 pages; a photograph of a boy jumping hurdles on the cover; contents: Features, Academic, Trips and Tours, Performing Arts, Pastoral, Community Activities, Staff News, Sport, Beyond Oakham, The Old Oakhamian Magazine, Foundation ; with various photographs of staff, pupils, house events, plays, sports, trips, buildings

Magazine named Oakhamian Magazine - The Magazine of Oakham School and The Old Oakhamian Club; 163 pages; a photograph of five girls performing Five Women Wearing the Same Dress on the cover; contents: Features, Academic, Performing Arts, Cover Story, Trips and Tours, Pastoral, Sport, Staff News, Old Oakhamian; with various photographs of staff, pupils, house events, plays, sports, trips, buildings

A prospectus for the school including names of trustees and staff, information on the school, boarding, the library, societies, terms, holidays, health, scholarships and prizes. Items A to C