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

A photograph of the Headmaster Tony Little attending an event in the Library, possibly an Old Oakhamian event, with Michael and Mary Stevens. Date is unknown.

A group of similar photographs (A to T) of the Headmaster Tony Little talking to members of the Decem outside Reception, probably in the early 2000s.

A photograph of the Headmaster Tony Little at an event with pupils. Date is unknown.