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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.

A collection which charts the various societies and activities available to pupils at Oakham School. Documents include photographic records and correspondence for different societies. Topics include chess, CCF/OTC, scouts, Duke of Edinburgh Award, Oligoi , Exploratory Society, and trips and expeditions.

The multiple series contain administrative documents for the various societies and certain series, such as Duke of Edinburgh Award and CCF/OTC have excellent photographic record of formal or informal events.

There is a particularly detailed series on Chess and the event of Gary Kasparov's visit to the school.

There is a good collection of shooting medals and trophies, kindly donated by Henry Blagg.

A certificate from the Diana Princess of Wales Memorial Award for Young People in recognition of students who have made a real difference to tackling bullying in their school communities awarded to Jerwoods Film Activity in the academic year 2005-2006.

List and photographs of pupils taking part in the Jerwoods Ski Trip to Italy in 2000. Seven pages A to G.

This file relates to the Jerwoods Ski Trip to Montgenève in 1999.

This sub-file contains photographs of pupils skiing and sledging on the 1999 Jerwoods trip to Montgenève.

A brochure for skiing lesson at Pontedilego and Tonale skiing resort.

A letter from Dr John Cheverton informing Parents of the kit-list for the Jerwoods Ski Trip in 1999.

This file contains administrative documents relating to the organisation of the Jerwoods Ski Trip to Tonale in 2000.