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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 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.

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 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 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.

Issue of the magazine 'Conference', vol.14, no.3, October 1977. Includes the article 'Twenty Years at Oakham' by John Buchanan (pp.19-23). Cover is a photograph of the interior of the Creative Design Centre at Oakham School.

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

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 series focusses on the headmastership of Grosvenor Talbot Griffith (1935-1958) and contains items relating to the life at School in the mid-20th century, its staff and pupils.

A brochure of photographs of Oakham School buildings, probably in the early 1930s.