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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 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.

An album containing photographs of the OTC and CCF at Oakham School. By some photos are name lists. Topics include first cam, inspection, First World War Cuttings, Jubilee Parades, Armistice Day, musicians, proclamation of King George VI, demonstrations of arms, letters and newspaper clippings.

A postcard of the inspection of the O.T.C. by Lord Roberts in 1912.

Photo of OTC Guard of Honour for Lord French, Oakham Railway Station 1917 (scan 00357) and two postcards of OTC Bordon, Inspection by Lord Roberts 1912 (scan 00352)

A photograph of the High Sheriff of Rutland, Major Herbert Whaley inspecting the C.C.F. cadets at the proclamation of Queen Elizabeth II in Market Place in 1952.

Photographs donated by John Fisher, at Oakham School from 1949 to 1957, who passed away in 2015