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A collection of documents, including photographs and commemorative plaques, relating to the School's cricket pavilions on Doncaster Close since the 19th century.

This sub-series focuses on the dedication of the Second World War memorial in the School Chapel in 1946.

This sub-series contains photographs of the boys in Deanscroft. It covers the whole history of the boarding since its inception in 1948, up to 1988 when the boys were transfered to the new Haywoods house.

This sub-series relates to the history of the Cadets at Oakham School since 1910. The bulk of the collection is made of photographs of inspection throughout the 20th century.

A collection of photographs and art work relating to the whole School Campus, in particular aerial photographs from 1937 of the School and the town, and a file of individual photographs of buildings around the campus. The oldest items in this sub-series date back to the 19th century.

This sub-series contains books used by pupils during services in chapel or books published by staff or Old Oakhamians and given to the school. A large part of this sub-series contains hymns books compiled by Rev T.C.H. Clare ('29).

This sub-series focusses on the every day running of School House. The bulk of the sub-series is punishment books and record books from the 1950s and 1960s.

This sub-series focusses on photographs of Oakham School 1st Shooting VIII, mostly during the 1950s and 1960s, as well as teams competing in the Ashburton Competition at Bisley.

This sub-series relates to Carol services and other Christmas celebrations held in the School Chapel or in Peterborough Cathedral, over a period of several decades. The bulk of the sub-series focuses on the 2000s onwards.

This sub-series related to the weekly services at the School Chapel since it being built in 1925. The registers record confirmation and baptism services as well as Carol services, evensong, matins and holy communion services.