This series focusses on the headmastership of Oliver Richard Sylvester Bull (1977-1984) and contains items relating to the life at School in the 1970s and 1980s, its staff and pupils. One of the files relates to Michael Stevens as Acting Headmaster for two terms in 1985.

This sub-file focusses on photographs of the Barraclough Hall since its construction in 1946.

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

A photograph showing boys reading books and the newspaper, sat outside the Deanscroft Beach Studies, probably in the 1960s. The photograph was taken by Photo-Reportage Ltd and the number of print is stamped on the back: 147807.

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.

This file focusses on writings by John Buchanan. Some items are articles, other items are his books.

This series focuses on the Junior House/Chapmans pupils and staff since its opening in 1910. It first comprised the Junior Department with facilities for boys boarders and classrooms. The house was renamed Chapmans in September 1960, after Frank Emerson Chapman, first Housemaster of the Junior House; it became a Senior House. Most of the series is made of photographs, house photographs as well as more informal photographs.

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.

This series focusses on the headmastership of Graham Smallbone (1985-1996) and contains items relating to the life at School in the 1980s and 1990s, its staff and pupils.

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