This series focuses on the history of Oakham School Chapel and religious services at the school. Early records dating from 1846 to the present day, content includes sub series on services, ephemera, the choir, the organ, the Chapel council and the millennium celebrations.

This collection consists of the mainly the non-paper aspects of the archives collection. The collection is random in its make up but has a good material collection which highlights the changing nature of the school's uniform. Items in this collection range in material type and stem from a variety of sources such as the Quatercentenary celebrations or items that were once used daily on the school grounds (such as building plaques or clock hands).

A collection of the musical works, correspondence and ephemera of former Oakham Music Director Peter Witchell. This series contains an excellent collection of full and single instrument scores.

This sub-fonds contains the complete collection of Red Books. These books contain a calendar of events for the upcoming term, lists of pupils and their houses, and lists of staff.

Material collected by Terrence Treanor throughout his time at Oakham School. Items include sheet music, orders of services, red books, Oakhamian magazines, photographs, registers, books and a school pin.

A collection of material from Anna Bentley's office including some school trophies, specially produced Oakham School dictionaries, entry books for the school, financial accounts, exam results, and correspondence. Most of the material in this collection relates to work completed in the marketing, administrative and foundation departments of the school.

This collection focuses on the administrative side of the school including admissions and trustees.

There is a rich collection of admissions books dating back to the 19th century alongside detailed notes of Trustees' committee minutes and development plans.

School inspections undertaken by external bodies are represented in this sub-fond and include some of the 19th century schemes which helped to found the school as one independent from Uppingham.

ADM/4 contains policy documents outlining the health and safety measures in the school.

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 covers the charity and outreach work undertaken by Oakham School's staff and pupils.

There are sub-series focusing on OSCA (the school's charity association), the Rutland Water Walk, Voluntary Action, and interaction with local prep schools.

Photographic and administrative material are particularly dominant in this sub-fonds.

This collection highlights the depth and breadth of the school's curriculum and pupil's work. The drama and music sub-series are particularly detailed with their collection of production stills and programmes.

CUR/7 contains reports relating to the school's teaching and curriculum alongside timetables for lessons and exams, and comprehensive examination results for GCSE, A Level and IB.

Throughout the series in this collection, there is material relating to events and trips undertaken by various departments to increase the extra-curricular activities of pupils.