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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 file focusses on photographs of the Music School throughout the years.

A blue photo album of Oakhamians and visitors: Schanschieff's Opening; Little, Alan Duncan MP, Wiliam Hague MP, Tom Lazur, Poppy Moore, Lord Sebastian Coe, Graham Lee, Martin Johnson, Ben Wheeler, Roger Blackmore, Philip Coates, Sheila Hardy, Jane Matthews, Margaret Cousins, Gary Kasparov, Pert, David Garner, Daniel Hyde, Matthew Pilling, Nicholas Branston, sports teams, pupils, a play

A photograph of the guests, staff and former staff, attending the celebration of the 50 years of Deanscroft/Haywoods in 1998.

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.

This series focuses on the history of the organs in the School Chapel, from the first one installed in 1930 to the current instruments built in 1993.

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.

Magazine named Oakhamian Magazine - The Magazine of Oakham School and The Old Oakhamian Club; 163 pages; a photograph of a girl and a boy and a bust on the cover; contents: News, Features, Academic, Trips and Tours, Performing Arts, Pastoral, Community Activities, Staff News, Sport, Beyond Oakham, Old Oakhamian, Foundation ; with various photographs of staff, pupils, house events, plays, sports, trips, buildings