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This series focusses on the headmastership of Grosvenor Talbot Griffith (1935-1958) and contains items relating to the life at School in the mid-20th century, its staff and pupils.

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 collection consists of material which highlights the history of Oakham School. This includes monographs and research by various authors, as well as films and others audio and video recordings.

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.

Two letter from Mildred F. Blunt, daughter of OO Edgar St John Blunt (1899), to John Barber asking him how to order copies of his book "The Story of Oakham School".

Two letter from Tony Earl congratulating John Barber on his book "The Story of Oakham School".

Two letters, from Trevor Case and Roger Blackmore to John Barber regarding the sums produced by the sales of signed copies of "The Story of Oakham School" to the Quatercentenary Appeal.

A newspaper cutting from The Independent reporting on letters revealing a previously unknown male love of Oscar Wilde, and on the debate concerning the frescoes in Old School. Hand-written note from Rod Smith to Graham Smallbone at the bottom of the article.

Two letters from Ron and Vivian to John and Betty Barber, regarding the purchase of "The Story of Oakham School".