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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 file focusses on photographs and artwork of John Buchanan, during his Headmastership (1958-1977) and various visits to the School in the 1980s and 1990s.

This series focusses on the headmastership of Oliver Richard Sylvester Bull (1977-1984) and contains items relating to the life at School in the 1970s and 1980s, its staff and pupils. One of the files relates to Michael Stevens as Acting Headmaster for two terms in 1985.

This file focusses on photographs of Graham Smallbone, during his Headmastership (1985-1996) and various visits to the School in the 1980s and 1990s.

A photograph of the Headmaster Graham Smallbone in 1994-1995.

A photograph of the Headmaster Tony Little giving a speech on his last School Assembly on Doncaster Close in 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 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.