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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.

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.

A collection of letters relating to OSEL courses, Activity Holidays and events in the 1980s.

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 Tony Little.

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 collection of documents has been filed by Jane Matthews, Senior Mistress of Oakham School. They related to H.M.C. Co-Educational Group Meetings of Senior Mistresses, resources for staff and pupils regarding wellbeing, maternity leave, health, and various correspondence. The collection spreads over a few years from the late 1980s to the mid-1990s.

This sub-file focusses on minutes of Parent/Teacher Committee meetings during the headmastership of Richard Bull (1978-1984).

This sub-series focuses on Chapel Council meetings and minutes from 1959 to 1979.

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