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This sub-series focuses on photographs of the Junior Day boys of Sargants House.

This series focuses on Peterborough House pupils and staff since its inception in 1966. Most of the series is made of house photographs, house magazines from the 1970s and various administrative documents.

A collection of photographs and art work of School House, and plans of the building.

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 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 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.

A collection of documents related to the Foundation of Oakham and Uppingham Schools by Archdeacon Robert Johnson, including several editions of the Statutes and Ordinances.

This series relates to the history of the Duke of Edinburgh's Award Scheme at Oakham School since 1973. Most of the collection focusses on the 1000th Gold Award celebrations in 2000 and the visit of Prince Philip.

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 is made of various items, such as informal photographs of the girls in Ancaster, house events, house prefects and miscellaneous objects. The bulk of the sub-series focuses on the 2000s.