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.

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.

A green hardback book containing lists of day girls for the Junior entry and Sixth form entry, from September 1987 to September 1997.

A blue notebook recording the performance of candidates who took the entrance examination in the 1970s. Six loose pages.

A green hardback book containing lists of day boys for the Junior Entry and Sixth form entry, from September 1987 to September 1998.

A red hardback book containing the registrations from 1980 and entries from 1983.

A brown notebook recording the performance of candidates who took the entrance examination between 1970 and 1978.

A yellow notebook recording the performance of candidates who took the entrance examination between 1959 and 1969.

A green hardback book containing short lists of boy boarders for the Junior Entry, from September 1987 to September 2000.