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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 letter (A) from John Buchanan to Michael Stevens regarding the arrival of girls at School and Michael and Mary becoming Housemasters of a girls' boarding house; enclosed is a writing by Michael Stevens on Co-Education, 'Some Random Jottings'.

A letter from Anthony Earl to the Headmaster, Dr Joe Spence, regarding the passing of John Buchanan and sharing memories of him. Two pages A and B.

A bound copy of several Old Oakhamian Magazines from 1985 to 1990.

A complete collection of bound books, gathering Old Oakhamian Magazines copies, from 1899 to 2002. Some books may contain issues of the Magazine that would be otherwise missing in the collection.

An almost complete collection of the Old Oakhamian magazines dating from 1897, until 2002. From that date, the Old Oakhamian has been included into the Oakhamian Magazine..

This file focusses on letters sent/received by John Buchanan, chiefly during his headmastership (1958-1977).

The Old Oakhamian Magazine, published in Autumn 1997. Contents: All Your Yesterdays; Oakham 1940-45; O.O. News; Gardens & Grounds; Marriages, Births & Deaths; Obituaries; Cricket World Trophy 1997.

A bound copy of several Old Oakhamian Magazines from 1994 to 2002.

This series focusses on documents relating to Brian Welford' career at Oakham School as Master-in-charge of Rugby in the 1970s and 1980s. Also contains documents relating to the history of rugby and Old Oakhamians, kept by Mr Welford in his personal files.