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.

This collection covers the history of all the libraries of Oakham School as well as the creation and daily working of the archives.

The Library series has material relating to each regeneration of the library (Smallbone, War Memorial). There is a rich photographic record of the opening and daily running of the Smallbone Library accompanied by administrative documents such as catalogues.

Under the Archives series, material cover correspondence with external readers and research into the history of the school and its pupils. There are also archive committee meeting minutes which show the evolution of the archives from its inception in 2010.

Hard cover album containing newspaper cuttings from each day of the First World War. First volume of a series of three, compiled by the Buchannan family.

Hard cover newspaper cuttings album relating to the First World War, with cuttings from "Punch" and other First World War ephemera, enclosing an Army certificate of identity of Nancy Bevan, a War Office letter regarding the resignation of Captain John Neville Buchanan, the Commission in Grenadier Guards of Second Lieutenant John Neville Buchanan and President Wilson's New Declaration of Freedom.

A letter from Bertie Bowes to John Barber regarding his holiday, his family and the letter HIS/1/2/4/47 sent to Tom Badgery.

A letter from Simon Schanschieff congratulating John Barber on his book.

Hard cover album containing newspaper cuttings from each day of the First World War. Second volume of a series of three, compiled by the Buchannan family.

Oakham School Magazine, recording the Winter term 1887 (published in Spring term 1888). Contents: The Concerts; The Unemployed of Ancient Rome; A Lycée at Caen; Cricket in its earliest forms; Notes on a Wimbledon Meeting; My First School; Football; Correspondence; School Notes. Nine double-pages A to I.

The Oakhamian Magazine, recording the Winter term 1945 (published in Easter term 1946). Contents: Roll of Honour; School News; The Library; J.T.C.; Scout Notes; War Memorial Fund; Music Notes; The Fall of the Shrines; Labour Notes; Hockey; Running; A Meeting between Lord Nelson and Napoleon; O.O. News; Cricket Fixtures. Six double-pages A to F.

The Oakhamian Magazine, recording the Spring term 1999. Contents: Editorial; Chapel; OSCA; Oxbridge; Concerts; Inner Cities Project; Drama; The Battlefields; The Total Eclipse of the Sun; Russia; California; GCSE Design & Technology; Sports; Houses.