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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.

This collection focuses on the administrative side of the school including admissions and trustees.

There is a rich collection of admissions books dating back to the 19th century alongside detailed notes of Trustees' committee minutes and development plans.

School inspections undertaken by external bodies are represented in this sub-fond and include some of the 19th century schemes which helped to found the school as one independent from Uppingham.

ADM/4 contains policy documents outlining the health and safety measures in the school.

A School list of staff and pupils for the Summer term 1915. Contents: Trustees; Teachers; Forms VI to I; Honours List; List of Exhibitions and Prizes gained during the year; Royal Drawing Society.

This sub-series focuses on the Dedication of the War Memorial Chapel on 29 October 1925.

This series focuses on various dedication and rededication services since the opening of the School Chapel. Most items are orders of services.

This series focusses on the headmastership of Francis Cecil Doherty (1929-1935) and contains items relating to the life at School in the early 20th century, its staff and pupils.

This series focusses on the headmastership of Grosvenor Talbot Griffith (1935-1958) and contains items relating to the life at School in the mid-20th century, its staff and pupils.

Oakham School Magazine, recording the Spring term 1924 (published in Summer term 1924). Contents: School Notes; Quinquennial Meeting of the Old Oakhamians; The New Classrooms and Laboratories at Wharflands; The Chapel; The Debating Society; The Cross Country Steeplechases; Cricket Fixtures and the Sports; Lectures; Dramatic Performances; O.T.C. Notes; Boxing; Fencing and Physical Training; Games Account - Balance Sheet for 1923. Five double-pages A to E.

Oakham School Magazine, recording the Spring term 1925 (published in Summer term 1925). Contents: School Notes; Fives; The School Museum; The Memorial Chapel; Steeplechase Races; The Sports; The Plays; Lectures; Correspondence; Games Account for 1924. Five double-pages A to E.

Oakham School Magazine, recording the Summer term 1926 (published in Winter term 1926). Contents: School Notes; O.T.C.; Under XIV Matches; The Chapel; Speech Day; Tempus Effugit; The Cricket Season; Correspondence; Games Account for 1925. Five double-pages A to E.