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This series is related to the buildings on the School campus and documents their history. Most of the collection is made of photographs and artwork, as well as architectural plans. Each sub-series focusses on a different building.

A book compiling the minutes of the Trustees' Financial Committee meetings.

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 subfonds contains the Archive's complete collection of Red books. These books contain a calendar of events for the upcoming term, lists of pupils and their houses, and lists of staff.

A complete collection of Red Books - School lists and Calendars since 1959. Red books give information regarding pupils, tutor groups, teaching and support staff, school calendar and events, school rules, future trips and dates. Only two Red Books were never published, Summer term 2020 and Spring term 2021 as the UK was in lockdown (COVID-19) and pupils were not at School and had lessons online.

This file focusses on various speeches given by John Buchannan during his headmastership and later. The bulk of the file is an almost complete collection of his Speech Day speeches.

A book compiling the minutes of the Trustees' Financial Committee meetings.

A small red book containing staff list, school list and school calendar for the Winter term 1964. Item belonged to Chris Frame.