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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 letter (A) from the Headmaster Graham Smallbone to be sent to Old Oakhamians after the Appeal launch. Attached are two lists (B and C) of recipients.

A photograph of the boys in Wharflands in the academic year 1969-1970 under the Housemaster John Barber. The names are written on the back.

This sub-series contains letters related to School House. The items relate to the 2004 naming ceremony of rooms in School House.

A letter from Simon Camamile to Jon and Kim Wills thanking them for the visit to School House and naming the rooms after his family.

A letter (A) from the Headmaster Graham Smallbone to be sent to Old Oakhamians regarding their contribution to the 1993 Development Plan. Attached are two lists (B and C) of recipients.

A letter (A) from the Headmaster Graham Smallbone to be sent to parents to invite them to a special buffet lunch, to contribute to the 1993 Development Plan; three lists of parents' names are attached (B to D).

A letter from John Buchanan, former Headmaster, to Old Oakhamians regarding the launch of the 1993 Development Plan Appeal.

A letter from Simon Schanschieff, Chairman of the Trustees, to potential donors.

A memo (A) from John Lake, Appeal Director, regarding approaches to prospective major donors and enclosing a draft letter (B) to be sent out.