A School list of staff and pupils for the Summer term 1915. Contents: Trustees; Teachers; Forms VI to I; Honours List; List of Exhibitions and Prizes gained during the year; Royal Drawing Society.

This file contains letters from the Headmaster Henry Price to parents and notices of past terms.

This file focusses on letters received/sent by the Headmaster Tony Little during his headmastership (1996-2002).

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

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

Extract from a 1940 prospectus, published in the Old Oakhamian Magazine. Content: Size; Staff; Fees; Curriculum; Timetable; Diet & Tuck boxes; Games; Activities outside the classroom; Day Boys. Three pages A to C.

This series focusses on the headmastership of Francis Cecil Doherty (1929-1935) and contains items relating to the life at School in the early 20th century, its staff and pupils.

A photograph of the Headmaster Graham Smallbone conducting a rehearsal of a staff performance, with David Smith singing and Philip Coates playing the cello. Date is unknown.

This series focusses on the headmastership of Grosvenor Talbot Griffith (1935-1958) and contains items relating to the life at School in the mid-20th century, its staff and pupils.

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.