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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 photograph of John Buchanan and other staff members leaving the Chapel, possibly taken in the late 1950s-early 1960s. The photograph was taken by Photo-Reportage Ltd and the number of print is stamped on the back: 147803. The number B3 is written on the photograph, in the bottom right corner.

Letters between the Headmaster Nigel Lashbrook and former teacher Greg Andrews regarding John Buchanan's letter to his friend Edward Leigh.

This file focusses on letters received/sent by the Headmaster Nigel Lashbrook during his headmastership (2009-2019).

A letter from the Headmaster Richard Bull to John Barber regarding his arriving at Oakham School, and gratitude to staff and Old Oakhamians in his first term.

A letter from former teacher Greg Andrews to the Headmaster Nigel Lashbrook regarding his time at Oakham School (A), and enclosing a letter from John Buchanan (B).

This file relates to the Headmaster's Annual report to the Trustees, from the 1950s to 1980s. The reports cover all aspects of School, academic, examination results, extra-curricular activities, Estates and Maintenance, staff and individual faculty report, vision for the future of the School. All reports are private and confidential.

A small red book containing staff list, school list and school calendar for the Spring term 1961; hand-written notations.

A small red book containing staff list, school list and school calendar for the Spring term 1962.

A small red book containing staff list, school list and school calendar for the Winter term 1962.