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 registrar's report for the year 1992, including numbers, boarding and day entries

A report from Michael Stevens, Second Master, for the year 1982/1983, including buildings, Ashburton Hall, Afternoon Activities, Examinations, Academic Attitudes, Environment. Discipline, Decem, School Marshal, Staff

A report from Rev John Darrall to be published in the Oakhamian Magazine on the charity events organised during the Winter term 1989, including houses charity events, a Non-Uniform Day, and other sponsored events.

A report from Rev John Darrall to be mentioned in the School Assembly on the charity events organised during the Spring term 1990, including the Valentine Disco, the Egotrip review and the appeal for 'get-well' cards.

A report from Rev John Darrall to be published in the Oakhamian Magazine on the charity events organised during the year 1991-1992, including the Rutland Water Walk, a hunger lunch, concerts, and houses events.

A account of a fire at Oakham School during the Doherty period.

Minutes of an OSEL meeting held on 25 October 1983 at the Headmaster's house. Contents: Minutes; Matters arising; Medical Congress, January 1984; Chess Tournament; Other April events; Activity Holidays 1984; Computer Weekends; Catering budgets and menus. Seventeen pages A to Q.

A headmaster's annual report fro the year 1982-1983, including numbers, Academic, Careers, A.V.A. Centre, Library, Art & Design, Music, Physical Education, Sports Hall, Playing Fields, Shooting, Drama, C.C.F., The Duke of Edinburgh's Award Scheme, Exploration Society, Scouts & Guides, Discipline and the Decem, Houses, Chaplaincy, Ashburton Hall, School Council, The Oakhamian, Senior and Middle School Societies, Voluntary Services, Sanatorium, Oakham School Nursery, Old Oakhamian Club; with appendix: A-Level results, leavers' destinations, report from the Computing Department

A headmaster's annual report fro the year 1983-1984, including numbers, Academic, Careers, A.V.A. Centre, Library, Art & Design, Music, Physical Education, Sports Hall, Playing Fields, Shooting, Drama, C.C.F., The Duke of Edinburgh's Award Scheme, Exploration Society, Scouts & Guides, Discipline and the Decem, Houses, Chaplaincy, Ashburton Hall, School Council, The Oakhamian, Senior and Middle School Societies, Voluntary Services, Sanatorium, Oakham School Nursery, Old Oakhamian Club; with appendix: A-Level results, leavers' destinations and academic scholarships