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.

This sub-file focusses on letters sent by the Headmaster John Buchanan to Richard Walker (Head Boy, 1971) and his father, John Walker.

A group of 430 slides taken by Jim Bride for the project "Sights and Sounds of Oakham School" between 1975 and 1976. Slides show staff and pupils in houses, on campus and in lessons, buildings, sporting events and other aspects of everyday life at school.

A bound copy of several Oakhamian Magazines from Winter 1976 to Summer 1980.

This file focusses on various photographs of Richard Bull during his headmastership (1977-1984).

This series focusses on the headmastership of Oliver Richard Sylvester Bull (1977-1984) and contains items relating to the life at School in the 1970s and 1980s, its staff and pupils. One of the files relates to Michael Stevens as Acting Headmaster for two terms in 1985.

This file contains various items created by Richard Bull or relating to his headmastership (1977-1984).

A book (A) by Bryan Matthews, 'The Book of Rutland', given to Nigel Straton as a formal present for the Nelson Firth prize, awarded at Speech Day 1980 by the Headmaster Richard Bull. Enclosed is a letter (B) from Richard Bull to Nigel Straton; and a letter (C) from R.M. Chillery to the School, who found the book in a charity shop.

The Oakhamian Magazine, recording the Winter term 1980 and Spring term 1981. Contents: Editorial; School News; Prize Winning essay; Letters to the Editors; Mathematics is more than a tool; Profiles; Exchange trip to Germany; Inspirations; Drama Reports; Music Reports; Society Reports; Sports Reports.

A bound copy of several Oakhamian Magazines from Winter 1980 to Winter 1983.