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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 series relates to Junior Boarding girls of Lincoln House. The house was built in 1974, as part of the new Jerwoods Campus for the Lower School. Most of the collection is made of the House photographs, as well as informal photograph of the girls in house events and sports competition, and programmes of some house events.

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

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 focusses on team photographs of cricket teams since 1860, first teams as well as second XI and junior teams.

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.

Bound copy of several Oakhamian Magazine; hard, black and red cover

Magazine named Oakhamian Magazine - The Magazine of Oakham School and The Old Oakhamian Club; 157 pages; a photograph of a girl in Kenya on the cover; contents: Features, Staff News, Trips and Tours, Academic, Performing Arts, Pastoral, Community Activities, Sport, Beyond Oakham, Foundation, Old Oakhamian, ; with various photographs of staff, pupils, house events, plays, sports, trips, buildings

Bound copy of several Oakhamian Magazine; hard, black and red cover