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This sub-series is made of various informal photographs of the boys in Deanscroft, especially in the 1960s. It also contains items related to the 50 years Anniversary celebration of Deanscroft & Haywoods House, including a tie designed for the special occasion.

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.

A group of original photographs and print-outs used as illustrations in John Barber's "The Story of Oakham School".

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-series is related to services held in the School Chapel since the laying of the Foundation stone in 1924.

This photographic series focuses on the history of the chapel since the laying of the foundation stone. It documents its building and opening, services held in the Chapel and objects used in everyday services.

A photograph of Oakham School cadets being inspected on Doncaster Close. The photograph was taken by Photo-Reportage Ltd and the number of print is stamped on the back: 157509.

A photograph of Oakham School cadets being inspected on Doncaster Close. The photograph was taken by Photo-Reportage Ltd and the number of print is stamped on the back: 157505.

A photograph of Oakham School cadets being inspected on Doncaster Close. The photograph was taken by Photo-Reportage Ltd and the number of print is stamped on the back: 157503.

A photograph of Oakham School cadets being inspected on Doncaster Close. The photograph was taken by Photo-Reportage Ltd and the number of print is stamped on the back: 157507.