This series focusses on the headmastership of Tony Little (1996-2002) and contains items relating to the life at School in the 1990s and early 2000s, its staff and pupils.

Staf handbook containing Introduction, Academic Matters, Student Welfare, Student Discipline, Social Matters, Games Policy, School Management Matters, Teaching Staff Information, Staff Development, Addenda. Items A to AW

A report from Michael Stevens, Second Master, for the year 1982/1983, including buildings, Ashburton Hall, Afternoon Activities, Examinations, Academic Attitudes, Environment. Discipline, Decem, School Marshal, Staff

A report from Michael Stevens, Second Master, for the year 1983/1984, including Entry, Houses, Discipline, Academic Attitudes, the Environment, Staff

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 series focuses on the boarding girls in Rushebrookes house. It was named after the first School Headmaster, Robert Rushbrooke. The first girls moved in in the Spring term 1980 but the building was officially open only on 22 November 1980. This series contains items related to the daily life of the girls in school and in house, as well as house photographs, mostly from the 2010s.

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.

The items in this series are related to Pastoral Care at Oakham School. Various topics include wellbeing, resources for tutorial, discipline and school rules, child protection and staff training.

This file focusses on matters of the Parent/Teacher Committee during the headmastership of Graham Smallbone.

This file focusses on matters of the Parent/Teacher Committee during the headmastership of Richard Bull.