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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.

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 collection of documents relating to the School's first cricket pavilion. It was built on the playing fields in the 19th century. It was then enlarged and renovated in 1931, when two changing rooms and a thatched roof were added. It unfortunately burnt in May 1970.

A collection of photographs of the School's first cricket pavilion, until it was destroyed in a fire in 1970.

A photograph of Headmaster Grosvenor Talbot Griffith in his office. The photograph was taken by Photo-Reportage Ltd and the number of print is stamped on the back: 808074.

A photograph of the Headmaster, G. Talbot Griffith, working in his office in the 1950s. The photograph was taken by Photo-Reportage Ltd and the number of print is stamped on the back: 286932.

A photograph of staff and pupils looking at a cricket match, sat by the New Pavilion in the 1950s. The photograph was taken by Photo-Reportage Ltd and the number of print is stamped on the back: 286913.

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 file focusses on photographs of G. Talbot Griffith, Headmaster of Oakham School.