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This series focusses on the history of the 21 Club at Oakham School.

Photo albums and scrapbooks compiled by members of staff throughout the years.

This series relates to Junior Day girls of Ancaster. 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 since the first year of Ancaster, as well as informal photograph of the girls in house events and sports competition.

This series focuses on the Day boys' house Barrow, founded in 1997. The main items are house photographs and handbooks.

This series relates to events organised by Oakham School Biology Society and the Medical Society.

The items in this series are books written and published by members of staff and are related to the history of Oakham School.

This series contains monographs written, updated and produced by Brian Needham, Honorary School Historian, regarding various themes of the history of Oakham School, its pupils and teachers.

This series focusses on documents relating to Brian Welford' career at Oakham School as Master-in-charge of Rugby in the 1970s and 1980s. Also contains documents relating to the history of rugby and Old Oakhamians, kept by Mr Welford in his personal files.

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.