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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.

This sub-series relates to the history of the Cadets at Oakham School since 1910. The bulk of the collection is made of photographs of inspection throughout the 20th century.

This series relates to the history of Oakham School Army, Naval and Air Force contingents since 1910, and of the Boy Scouts. Most of the collection is made of photographs from the mid-20th century.

Order of service for the Remembrance Sunday service for the Centenary of the Armistice in the School Chapel on 11 November 2018.

The sub-series focuses on the Humfrey Family, more particularly on Stuart and Douglas Humfrey, and include "The Humf Letters".

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2013 and Spring term 2014. Contents: News; Features; Academic; Trips and Tours; Performing Arts; Pastoral; Community Activities; Staff News; Sport; Beyond Oakham; Old Oakhamian; Foundation.

The Oakhamian Magazine and Old Oakhamian Magazine, recording the Summer term 2014. Contents: News; Features; Academic; Performing Arts; Jerwoods; Trips and Tours; Pastoral; Community Activities; Staff News; Sport; Beyond Oakham; Old Oakhamian; Foundation.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2014 and Spring term 2015. Contents: News; Features; Academic; Trips and Tours; Performing Arts; Pastoral; Community Activities; Staff News; Sport; Beyond Oakham; Old Oakhamian; Foundation.

The Oakhamian Magazine and Old Oakhamian Magazine, recording the Summer term 2015. Contents: News; Features; Academic; Cover Story; Performing Arts; Jerwoods; Trips and Tours; Pastoral; Community Activities; Sport; Staff News; Beyond Oakham; Old Oakhamian; Foundation.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2015 and Spring term 2016. Contents: News; Feature; Academic; Trips and Tours; Performing Arts; Cover Story; Pastoral; Community Activities; Staff News; Sport; Beyond Oakham; Old Oakhamian; Foundation; The O.O. Interview.