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This series focusses on the headmastership of Rev Edward Vere Hodge (1879-1902) and contains items relating to the life at School in the late19th century, its staff and pupils. The series contains some of the earliest photographs of Oakham School's collection.

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.

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

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.

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 from Andrew to John Barber regarding his book "The Story of Oakham School" and sharing memories of his time at school as a pupil.

A letter from O.O. W.J. Thompson ('23) to Brian Welford regarding rugby matches he was involved in and various Old Oakhamians who played in the rugby team in the 1920s. Four pages A to D.

A letter from Robert Stevens, President of Haverford College, thanking John Barber for sending a copy of his book "The Story of Oakham School" and sharing some memories of his time at school as a pupil.

A letter from Peter North, Principal of Jesus College, Oxford, to John Barber regarding his book "The Story of Oakham School".

A letter from Patrick Wilson to Stephen Kimbell asking for a small contribution to the 1993 Appeal. Three pages A to C.