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.

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 series contains monographs written, updated and produced by Brian Needham, Honorary School Historian, regarding various themes of the history of Oakham School, its pupils and teachers.

A monograph written and updated by Brian Needham on the history of the Duke of Edinburgh Award at Oakham School from 1960 to 2015. Contains a history of the Award at the school and includes a list of the award winners.

A monograph written by Brian Needham on the Oakham School Exploration Society and the overseas expeditions from 1979 to 2012.

A list of medical emergencies and how to deal with them and a list of pupils with medical conditions.

A letter from the School's Bursar, Trevor Case, to Parents directly concerned with the Papua New Guinea Expedition regarding the cost of this expedition (page A), enclosing an annex detailing the income & expenditure for the trip, the money received after fund raising initiatives and an analysis of costs on a per capita basis (page B).

Oakham School Magazine, recording the Summer term 1888 (published in Winter term 1888). Contents: The Speech Day; Organ recital; The Italian Exhibition; Bound for Australia; Handel; Old Oakhamian Club; Poetry; Cricket; School Notes. Eleven double-pages A to K.

Oakham School Magazine, recording the Winter term 1890 (published in Spring term 1891). Contents: The Concerts; Lutterworth; Golf; A Visit to the Post Office; Poetry; Western Australia; Paperchases; Old Oakhamian Club; Entertainment; Football; School Notes. Nine double-pages A to I.

Oakham School Magazine, recording the Summer term 1890 (published in Winter term 1890). Contents: Speech Day; The Speech Day Sermon; Four Oakham men afloat; Newstead Abbey and Park; Western Australia; Poetry; Cricket; School Notes. Eleven double-pages A to K.