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Stretching back to the headmastership of Dr. Doncaster, this collection comprehensively covers the correspondence, publications, photographs and other ephemera of the headmasters of Oakham School up to the present day. For many of the headmasters, correspondence and rolls calls are a significant theme in their series.

This collection also contains an excellent record of speeches and sermons given by G. Talbot Griffiths and John Buchanan.

The final series on reports covers the headmaster's, deputy headmaster's and registers writings on the state of the school, including topics such as building and estate development, admissions, the curriculum, examination results, and Old Oakhamians.

A letter from Adam Lowe, a volunteer Special Constable with Leicestershire Constabulary, to Nigel Lashbrook, Headmaster of Oakham School, regarding a talk on Rutland County Police at the Rutland County Museum and research on the town prison.

A photograph of The Duke of Gloucester, alongside the Headmaster Nigel Lashbrook and another officer, on 6 May 2010.

A collection of documents relating to the BAFS Pavilion, built on Doncaster Close, on the site of the original cricket pavilion. It was opened on 24 May 2014, on Speech Day, by Mike Gatting. It was named BAFS after O.O. Brian Smith (‘54), captain of the school’s unbeaten first Rugby XV, Hockey XI and Cricket XI teams.

A newspaper cutting from the Rutland & Stamford Mercury reporting on the opening of BAFS cricket pavilion on 30 May 2014.

An almost complete collection of Oakham School magazines dating from 1884. Some editions are available as individuals whilst others can be found in larger bound volumes. There is also a collection of the Old Oakhamian magazine which is a separate school magazine for Old Oakhamians and their news.

This magazine covers all aspects of school life. Sporting, academic, and artistic achievements of the pupils are celebrated alongside news updates from various departments. In later issues, c. 1980s, houses are given space to announce news and in house achievements.

Sporting records are a key component of the magazine since its inception and there are accounts of matches (including scores and teams) in each edition. Again, since the 1980s, focus has shifted to also include all of the teams that compete for the school, instead of just focusing on the A team.

Images and photographs start to appear in the magazines from the 1970s and the magazine was first printed fully in colour in the 1990s.

A green minute book recording minutes of working party meetings and general meetings of the Oakham School Foundation from the 2000s.

This collection draws together material produced for and by the marketing department of Oakham School. Particular strengths of the collection include press cuttings and publication material (prospectuses, handbooks, maps etc.).

Press cuttings from multiple local and national newspapers have been collected together by marketing staff, gathering together news of Old Oakhamians.

Publications contain material produced for new admissions into the school and contain detailed information about uniform, curriculum, pastoral care, and general daily life of the school.

A letter from the Headmaster Nigel Lashbrook to Parents at the end of Spring term 2019. Contents: Examinations; Gala Concert; Decem; Brexit.