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 collection focuses on the staff who have worked for Oakham School over the years. Material focuses on not only training and teaching, but staff wellbeing, pay and benefits.

There are two series which focus on notable members of staff from the school's history: Jon Wills and Brian Welford. Material for these staff members have been collected by themselves and other members of staff.

Recruitment series includes jobs descriptions for various positions, both teaching and support staff, in the school.

There is a strong collection of policies an guidance for teachers in completing the many administrative and teaching jobs expected.

This is focussing on Oakham School Enterprises LTD, since its creation. This file is chiefly made of legal documents and letters.

A collection of letters relating to OSEL courses, Activity Holidays and events in the 1980s.

A letter from Alan Grieve to Roger Blackmore regarding the minutes of OSEL meetings and raising two points on Activity Holidays and Computing courses. Two pages A and B.

A letter from Alan Grieve to Roger Blackmore regarding the latest meeting of OSEL board.

A letter from Roger Blackmore to Alan Grieve regarding the minutes of an OSEL meeting and the publicity for the upcoming Chess Congress.

A letter from Roger Blackmore to Alan Grieve regarding the agenda for the next OSEL meeting and enclosing notes and initial comments on the questionnaires, accommodation, courses and other activities. Six pages A to F.