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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 photographs of the Day Boys in Hodge Wing in the 1950s and 1960s.

This sub-series focuses on photographs of girls in Orchard Close and Buchanans House, mostly in the 1990s and early 2000s. It also contains photographs of the Sixth Form cohort.

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 focusses on photographs of various Chess tournaments and other events held at Oakham School.

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 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 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.

This sub-series focuses on the history of the 1993 Organ in the School Chapel. After the 1930 organ expired and was replaced by a computer organ in the 1980s, the headmaster Graham Smallbone commissioned for a new organ to be built. Some items highlight the various proposals, the correspondence focuses on the building and installation of the organ and the photographic file finally shows the organ in Chapel.

A series of photos of frescos in Shakespeare Centre by Mary Sargant Florence (including some images of Old School before it was the Shakespeare Centre). Also included is a letter from Margaret Camester which attaches extract of book to be published about the women's peace movement of 1915 (which contains a pamphlet by Mary Sargant Florence called 'Militarism versus feminism' and biography of her). At the back is a sheet which includes the inscribed stone over the old school door and a translation of it.