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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.

The Oakhamian Magazine, recording the Summer term 1991 (published in October 1991). Contents: People - Places - Events; Co-Education; Festival Music; Drama; Peterborough to London by Kayak; Speech Day; A Day in the Life Of Oakham School; Aerobathon; Music; Sport.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Spring term 2007. Contents: School Notes; Features; Academic; Pastoral; Sport; Beyond Oakham; Foundation; Old Oakhamian.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Spring term 2008. Contents: Features; Academic; Pastoral; Sport; Beyond Oakham; Foundation; Old Oakhamian.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Spring term 2009. Contents: Features; Staff News; Academic; Pastoral; Sport; Beyond Oakham; Foundation; Old Oakhamian.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2017 and Spring term 2018. Contents: Features; Academic; Performing Arts; Cover Story; Trips and Tours; Pastoral; Sport; Staff News; Old Oakhamian.

An almost complete collection of the Old Oakhamian magazines dating from 1897, until 2002. From that date, the Old Oakhamian has been included into the Oakhamian Magazine..

The Old Oakhamian Magazine, published in April 1994. Contents: Sportsman takes over; O.O. Network; Announcements & News; Oakham 93; O.O. News; Lives Remembered; K.E.M.; Land of Smiles; O.O. Sport; O.O. Day.

Order of service for the marriage of Kim Mortimer and Jon Wills, P.E. teachers, in the School Chapel on 23 July 1983.

Order of service of the service of thanksgiving for the lives of Anna Haefeli and Anastasia Besedovska held at the Chapel on 17 January 2015.