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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 guests and participants at the 1984 International Junior Chess tournament organised as part of the Quatercentenary celebrations.

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.

Two similar photographs (A and B) of former Headmaster John Buchanan and the Visitor, John Jerwood, attending a chess tournament in the Sports Hall in 1984.

Two photographs (A and B) of former Headmaster John Buchanan and the Visitor, John Jerwood, attending a chess tournament in the Sports Hall in 1984. Photograph A is in colour; photograph B is in black and white.

This contains photographs of the visit of HRH The Duke of Edinburgh and the celebration of the 1000th Gold Awards being awarded at Oakham School.

A photograph of Oakham School staff in the late 1950s/early 1960s, under Headmaster John Buchanan.

A photograph of Oakham School staff in the late 1950s/early 1960s, under Headmaster John Buchanan.

A photograph of Oakham School staff, possible in 1969 or 1970, under Headmaster John Buchanan.

A photograph of Oakham School staff in the mid to late 1960s, under Headmaster John Buchanan.