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 collection focuses on the staff who have worked for Oakham School over the years. Material focuses on not only training and teaching, but staff wellbeing, pay and benefits.

There are two series which focus on notable members of staff from the school's history: Jon Wills and Brian Welford. Material for these staff members have been collected by themselves and other members of staff.

Recruitment series includes jobs descriptions for various positions, both teaching and support staff, in the school.

There is a strong collection of policies an guidance for teachers in completing the many administrative and teaching jobs expected.

This series focusses on photographs of teaching and support staff throughout the years. The bulk of the collection is individual photographs of staff from the 1990s.

This file focusses on various photographs of individual teaching and support staff. The bulk of the file date from the 1990s.

This series focuses on School House pupils and staff in the 20th century. Most of the series is made of house photographs, various informal photographs as well as records books and punishment books.

This sub-series focusses on various photographs of the pupils and staff of School House as well as various documents related to the history of the house.

This sub-series focuses on photographs of boys in School House since the 1940s.

This file focusses on letters sent/received by John Buchanan, chiefly during his headmastership (1958-1977).

A bound copy of several Oakhamian Magazines from 1964 to 1967. Item A has a black cover; item B has a brown cover.

Two bound copies of several Oakhamian Magazines from 1968 to 1971. Item A has a black cover; item B has a brown cover.