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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.

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 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.

A group of four articles entitled the 'New light on Oakham History' by W.L. Sargant which were printed in a newspaper. The articles are based on research undertaken by Mr Sargant in the Muniment Room of Westminster Abbey and written whilst he lived in Sidmouth, therefore in the late 1940s-early 1950s. Four pages A to D.

A newssheet from the Headmaster Richard Bull listing the achievements and events of the Summer term 1984, including future term dates.

A newssheet from the Headmaster Richard Bull listing the achievements and events of the Winter term 1984.

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.

A history titled 'Oakham Through the Centuries', written by former Headmaster W.L. Sargant. Contents: from prior to the Saxon occupation to the end of the 18th century. Hand-written note on the cover reading 'With best wishes for the new year, W.L.S.' Five double-pages A to E.

This series focusses on the headmastership of Oliver Richard Sylvester Bull (1977-1984) and contains items relating to the life at School in the 1970s and 1980s, its staff and pupils. One of the files relates to Michael Stevens as Acting Headmaster for two terms in 1985.

An article titled 'The Pattern of the Anglo-Saxon Settlement of Rutland' by W.L. Sargant, published in the journal 'Geography. Three pages A to C.