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".

This series focusses on the headmastership of John David Buchanan (1958-1977) and contains items relating to the life at School in the 1960s and 1970s, its staff and pupils. The bulk of the series consists of books, publications, letters, speeches and sermons written by Mr Buchanan himself.

This file focusses on letters sent/received by John Buchanan, chiefly during his headmastership (1958-1977).

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.

A photograph of a dinner at Oakham School in 1963, showing pupils of Hodge Wing and School House in the Dining Room. The photograph was taken by Photo-Reportage Ltd and the print number is stamped at the back: 862873.

This file focusses on letters received/sent by the Headmaster Graham Smallbone during his headmastership (1985-1996).

This series is related to outreach events organised outside lesson timetable, promoting activities at school, supporting the local community and attending events with/for other schools. This series places Oakham School at the centre of the local community.

Seven photographs taken by Photo-Reportage Ltd, at various dates, in the 1960s. The photographs show pupils in the School House dining room, in their dorms and in the quad.

A booklet produced by Davis Langdon & Everest for Oakham School on a first estimate for the Oakham Innovation Centre. Contents: Comparison between options, Summary of Estimate, List of drawings and other information, Exclusions, Schedule of Areas, Design Reserve and Contract Contingency, Inflation an Programme, Detailed analysis of construction costs.