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 highlights the achievements of Old Oakhamians after they have left Oakham School.

This collection charts the history and activities of the Old Oakhamian Club. It has excellent records of dinners and events thrown by the club such as reunions, international dinners and Oakham events. Most of the documents are administrative, but there are photographs and correspondence material too.

There are good records on the school's foundation and the club's golfing society. Most of the material has been produced by the Old Oakhamian club or the foundation. Thus, there is a good record of publications and marketing material relating to these events.

An article published in The Independent on Sunday on the publication of a new book, "Wisden on the Great War", and focussing on the Oakham School 1st cricket XI of 1914 and the five boys in the team who fell in the Great War. The article is spread on two pages, numbered A and B.

A letter from Simon congratulating John Barber on his book "The Story of Oakham School".

A letter from John Buchanan congratulating John Barber on his book "The Story of Oakham School".

A letter from Gaie Owen thanking John Barber for sending his book "The Story of Oakham School".

A letter from David J. Woodhead, National Director of the Independent Schools Information Service, to Graham Smallbone regarding the passing of the Children's Act and its consequences in cases of abuse nationwide, enclosing an ISJC circular notifying of its implications. Three pages numbered A to C.

A list of the Senior Mistresses members of the H.M.C. Co-Educational Schools Group, organised by divisions.

A list of the Senior Mistresses members of the H.M.C. Co-Educational Schools Group. Two pages numbered A and B.