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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.

This series focusses on the headmastership of Tony Little (1996-2002) and contains items relating to the life at School in the 1990s and early 2000s, its staff and pupils.

This file focusses on photographs of Tony Little, during his Headmastership (1996-2002).

A group of seven similar photographs (A to G) of the Headmaster Tony Little working at his desk in 2001.

A group of negatives (A), index (B) and photographs (C to AK) of the 30 years of Co-Education celebration outside the Library, gathering former headmasters and their wives, and the first girls' cohort.

A group of negatives (A) and similar photographs (B to O) of the Headmaster Tony Little in front of College House.

A photograph of the Headmaster Tony Little, his wife Jenny and their two dogs. Date is unknown.

A photograph of the Headmaster Tony Little, Alan Grieve and David Woodcock, Head of Music. Date is unknown.

A group of two indexes (A and B) and negatives (C) of various photographs of the Headmaster Tony Little and a concert in Chapel. Date is unknown.

A photograph of the Headmaster Tony Little and members of the 2001 Decem, including the Head Boy and Head Girl, Guy Hurwood and Kate Campbell, and Katie White and James Bowerman.