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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.

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

This sub-series relates to the history of Old School, oldest building of Oakham School, in Cutts Close park. It is made of a collection of photographs and art work; of newspaper cuttings and letters, mostly relating to the debate concerning the refurbishment of the building and preserving the frescoes painted by Mary Sargant Florence.

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.

A collection of reports and financial statements, and letters, related to the activities of Oakham School Enterprises Ltd (OSEL), spanning from 1978 to 1995.

A book recording dates and times of services in the School Chapel, including the initials of the officiant, the attendance, the preacher, and the collections from Spring term 1978 to Summer term 1991.

Minutes of an OSEL meeting held on 25 October 1983 at the Headmaster's house. Contents: Minutes; Matters arising; Medical Congress, January 1984; Chess Tournament; Other April events; Activity Holidays 1984; Computer Weekends; Catering budgets and menus. Seventeen pages A to Q.

A bound copy of several Oakhamian Magazines from Spring 1984 to Summer 1987.

The Oakhamian Magazine, recording the Winter term 1985 and Spring term 1986. Contents: Editorial; School News; Charities and Community Service; Feature "Little Boxes"; Drama; Music; Societies; Adventures Abroad; C.C.F. and Duke of Edinburgh Award Activities; Sport.

A bound copy of several Old Oakhamian Magazines from 1985 to 1990.