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This collection contains material relating to the history of the houses and their pupils. Each series is focused on a different house and many contain rich and detailed photographic records of houses year by year. Some houses are more detailed than others.

Other highlights of this collection include house handbooks, which help to induct a pupil into a house and its daily routine; photographs of daily life, including house events and leisure time; and administrative documents such as house diaries which record the calendar of house events, achievements of pupils, and accounts of incidents.

Included in this sub-fonds are houses which are no longer in existence such as Johnsons and Ruddles.

This file contains booklets produced to celebrate leaving staff's time at Oakham School, and reminiscences from former staff.

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 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 list of attendees at the Leavers lunch in 2006. Two pages A and B.

Several documents containing a list of staff walking, driving, marshalling or manning the checkpoints, with emergency contacts and information for staff on safety and the route. Eleven pages A to K.

This file focusses on matters of the Parent/Teacher Committee during the headmastership of Tony Little.

A list of the Housemasters of School House from 1951 to 2001.

A letter from the Headmaster Tony Little to Parents regarding a review of the Summer events, before the start of Winter term 1999. Contents: Timings of the first day of term; Expeditions; Maintenance work; Public Examination Results.

This sub-file contains various photographs of Jim O'Kane.