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A collection of photographs of the Barraclough Hall since its construction in 1946. Once a warehouse at the terminus of the Canal on Ashwell Road, later converted into stables, the Barraclough Hall was named in honour of Mrs Barraclough, benefactor to the school, and in memory of her late husband, Norman Barraclough (OO, 1883). At the west end was the stage and the theatre would seat about three hundred and fifty people. Other features included a traditional long hall, raked stage and Proscenium Arch. The opening ceremony took place on 20 June 1953.

A collection of photographs and post cards of Deanscroft house, documenting the improvements and changes of the boarding house since its acquisition in 1948.

This file contains various photographs of the Ashburton building, formerly the Haywood building on Church Street, throughout the years.

This file focusses on photographs of the various Science buildings and laboratories throughout the years.

This file focusses on photographs on the School Campus throughout the years. Some photographs are of the whole campus, in particular aerial photographs taken by Aerofilms Ltd, and some are collection of individual buildings, taken by Companies or individuals.

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.

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

This file focusses on photographs of various Inspections of the Cadets and contingents, as well as group photographs of full contingents since the early 20th century.