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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 photograph of the Day Girls in Ancaster in the academic year 2018-2019 under the Housemistress Alison Petit. Names of pupils and staff are written under the photograph.

A sheet of paper advertising the grand yo-yo competition on 17 October 1998, with names of pupils who signed up.

A sheet of paper with a drawing of a netball court and names of pupils and their positions on the field.

A programme for the Jerwoods Sports Day on 30 June 1999, including a list of events, the house teams, the 1998 results, the rules of competition and a list of the officials. Three double-pages A to C.

A programme for the Jerwoods Sports Day on 27 June 2001, including a list of events, a list of the officials, the house teams, the 2000 results, the rules of competition and the 2001 competition results. Three double-pages A to C.

A programme for a Jerwoods Concert on 12 June 2001 in the School Chapel, including a list of the musical numbers and a list of the performers and various bands.

A programme for the Jerwood Wind Band and Intermediate String Orchestra concert in Chapel on 22 January 2002, with list of performers and musical numbers.

An email from Jo Welch to Anne Rawlins, Jane Carnell, Michelle Northcott, Stephanie Mayes, Charles Welch and Nick Davenport regarding the Girls' Jerwoods Cross Country results in March 2002.