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This sub-series contains photographs of the exterior and interior the School memorial Chapel throughout the years. The earliest photographs showed the chapel being built in 1924-1925.

A photograph of the south front and stairs of the Chapel, possibly taken in the late 1950s-early 1960s. The photograph was taken by Photo-Reportage Ltd and the number of print is stamped on the back: 157535.

A photograph of the chancel of the Chapel, showing the altar and the cross, taken around 1966. The photograph was taken by Photo-Reportage Ltd and the number of print is stamped on the back: 862845.

A photograph of John Buchanan and other staff members leaving the Chapel, possibly taken in the late 1950s-early 1960s. The photograph was taken by Photo-Reportage Ltd and the number of print is stamped on the back: 147803. The number B3 is written on the photograph, in the bottom right corner.

This sub-file contains various photographs of the 'Big Four', G.R. Liebert, K.R. Bowes, John Moore and R.F. Duesbury.

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.

This series focuses on School House pupils and staff in the 20th century. Most of the series is made of house photographs, various informal photographs as well as records books and punishment books.

A photograph of a dorm in School House. The photograph was taken by Photo-Reportage Ltd and the print number is stamped at the back: 862841.

A photograph of pupils climbing the stairs from the quad. The photograph was taken by Photo-Reportage Ltd and the print number is stamped at the back: 157564. A number is written in the bottom right corner: 64.

This series relates to the history of Oakham School Army, Naval and Air Force contingents since 1910, and of the Boy Scouts. Most of the collection is made of photographs from the mid-20th century.