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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.

An order of service for a service of thanksgiving for the life of Reverend Terence Gerald Treanor ('47) in the School Chapel on Saturday 29 September 2018.

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 Jon Wills, Chairman of the Old Oakhamian Club, to Lewis Moody ('97) regarding attending the opening of a room named after him in School House.

A letter (A) from Graham Smallbone, Headmaster, Simon Schanschieff, Chairman of Trustees, and Rev Terence Treanor, Honorary Secretary of the Old Oakhamian Club, to former pupils who were at Oakham during John Barber's years with the School regarding celebrating his eightieth birthday and the Barber Archives. Attached is a reply slip (B).

Correspondence relating to the Oakham School 1993 Development Plan.

Correspondence relating to John Barber's eightieth birthday and the Barber Archives.

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.

Four sample letters (A to D) from the Headmaster Graham Smallbone to be sent to potential donors to support the 1993 Development Plan.

Four identical letters (A to D) from Headmaster Graham Smallbone and four other members of staff - Roger Blackmore, Nigel Webb, John Buchanan and Rev Terence Treanor- to Old Oakhamians. Attached is a mailing list (E).