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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.

This series focusses on the headmastership of Francis Cecil Doherty (1929-1935) and contains items relating to the life at School in the early 20th century, its staff and pupils.

Email correspondence (A) between Jill Harris and Shelly Bojcic, Educational Consultant at Hodder Education, regarding her visiting the school and enclosing a poster (B) advertising Hodder Education's Educational Resources display.

This collection highlights the depth and breadth of the school's curriculum and pupil's work. The drama and music sub-series are particularly detailed with their collection of production stills and programmes.

CUR/7 contains reports relating to the school's teaching and curriculum alongside timetables for lessons and exams, and comprehensive examination results for GCSE, A Level and IB.

Throughout the series in this collection, there is material relating to events and trips undertaken by various departments to increase the extra-curricular activities of pupils.

Seven letters regarding the opening of the Rutland Crown Court in Oakham Castle on 13 January 1992.

A collection of photographs and art work of College House, formerly the Old Vicarage, which was the Sanatorium before becoming the first girls' boarding house in 1971. Also contains a large file on the architecture and history of the building.

This collection covers the charity and outreach work undertaken by Oakham School's staff and pupils.

There are sub-series focusing on OSCA (the school's charity association), the Rutland Water Walk, Voluntary Action, and interaction with local prep schools.

Photographic and administrative material are particularly dominant in this sub-fonds.

This sub-series contains photographs of the exterior and interior the School memorial Chapel throughout the years. The earliest photographs showed the chapel being built in 1924-1925.

A copy of Oakham School Common Room application for the renewal of Club Registration Certificate under the Licensing Act 1964.