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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 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.

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

Notices compiled at the end of the Winter term 2017 and sent to Parents. Contents: Change of status requests; Form 3 Registrations; Siblings enquiring for Form 6 entry; Non EEA pupils; Medical Centre; Music Dates; Oakham Choral Society; Term Dates; Art Calendar; Parent Portal; School Archives; Art; Staff Changes. Two pages A and B.

A letter from the Headmaster Nigel Lashbrook to Parents at the end of Summer term 2019, his last at Oakham School.

A letter from the Headmaster Nigel Lashbrook to Greg Andrews regarding John Buchanan's letter to his friend Edward Leigh.