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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.

The financial regulations policy for Oakham School, the Foundation and OSEL, including staff responsibilities, risk assessment, budget, planning, fraud and corruption, reporting, income, expenditure and income generation.

A poster advertising training sessions for squash in the Summer term 2021. The item was pinned on the notice board in house.

A photograph of teachers sat around a table in Old Hall, for a meeting or training. Date is unknown.