This collection highlights the work and life of Oakham School pupils both during and after their time at the school. The collection has an excellent representation of the careers, work, and exam aspect of school life, including examination results, leaver destinations, work experience and information on Project 20/20.

There are detailed records on the council, Decem and prefects, particularly in their recruitment, meeting minutes, and handbooks.

In several of the series, there is a strong photographic collection illuminating the rich daily life of the school and its pupils. This is shared alongside copies of pupil magazines, arts calendars, and records of pupil achievements.

A video tape (22 minutes) produced by Geoffrey Isles Photography, containing William Winter's photographs taken between 1950 and 1955. William Winter was a Resident Tutor in Wharflands and a teacher of English and History.

Oakham School Magazine, recording the Spring term 1904 (published in Summer term 1904). Contents: Editorial; School Notes; Prefect Board; The Debates; The Sports; Cricket; Hockey; Correspondence. Seven double-pages A to G.

A bound copy of several Oakhamian Magazines from 1900 to 1904.

A bound copy of several Oakhamian Magazines from 1902 to 1910.

A photograph of Martin Debenham talking to a prefect. Date is unknown.

This series focusses on the headmastership of Rev Edward Vere Hodge (1879-1902) and contains items relating to the life at School in the late19th century, its staff and pupils. The series contains some of the earliest photographs of Oakham School's collection.

A roll call for School House, Mr. Scriven's, Mr Williams', Bank House and the Day Boys in Winter term 1887. One name has been hand-written in Form VI.

A School list for the Spring term 1902 for School House, Red House and the Day Boys.

A roll call for School House and Mr. Scriven's in Winter term 1885, with hand-written notations and "E.C. Jeffery" stamped several times at the back.