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This series focusses on the headmastership of Graham Smallbone (1985-1996) and contains items relating to the life at School in the 1980s and 1990s, its staff and pupils.

This file focusses on letters received/sent by the Headmaster Graham Smallbone during his headmastership (1985-1996).

This file focuses on the correspondence between Oakham School and organ builders, including Peter Collins Ltd, since 1990 and giving an insight as to the building and installation of the new organ in the School Chapel. Some letters were sent/ received between the Headmaster Graham Smallbone and the White and Lea families regarding an inscription in memory of David White and Henrietta Lea.

A report from Rev John Darrall to be published in the Oakhamian Magazine on the charity events organised during the year 1991-1992, including the Rutland Water Walk, a hunger lunch, concerts, and houses events.

This series relates to various annual reports presented to the Trustees, including Headmaster's reports, Registrar's reports and Second Master's reports. The series spans over three Headmasters, John Buchanan, Richard Bull and Graham Smallbone.

A report from Rev John Darrall on the charity events organised during the Spring term 1989, including the Valentine Disco, Red Nose Day, concerts, houses events and listing the charities supported by the school.

A report from Rev John Darrall to be shared in the School Assembly on the charity events organised during the Spring term 1989.

A report from Rev John Darrall to be published in the Oakhamian Magazine on the charity events organised during the Summer term 1989, including house events, a piano marathon and detailing the money raised for the charities supported by the school.

A report from Rev John Darrall to be published in the Oakhamian Magazine on the charity events organised during the Winter term 1988, including concerts, Drama performances, Non-Uniform Day and various houses events.

An end-of-term summary from Rev John Darrall on the charity events organised during the Winter term 1988.