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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 series focusses on the headmastership of Nigel Lashbrook (2009-2019) and contains items relating to the life at School in the 2010s, its staff and pupils.

This file focusses on writings by the Headmaster Nigel Lashbrook.

Issue no.6 of 'Insight. The Magazine of HMC' published in June 2016, containing an article written by the Headmaster Nigel Lashbrook on Learning p.21 and an article written by former Headmaster Dr Joe Spence on Learning p.20.

This file focusses on programmes, invitations and menus to various events under Dr Joe Spence's headmastership.

This series focusses on the headmastership of Dr Joe Spence (2002-2009) and contains items relating to the life at School in the 2000s, its staff and pupils.

A menu for the Headmaster's Dinner on 25 February 2009.

This file focusses on photographs of Dr Joe Spence, during his Headmastership (2002-2009).

This file focusses on obituaries and tributes written in memory of former Headmaster, John Buchanan, as well as letters from friends and family.

Two letters (A and B) between Jeremy Tomlinson, Bursar & Clerk to the Trustees, and Philip Robson at Daltons Solicitors, regarding the estate of the late John David Buchanan.