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This series contains monographs written, updated and produced by Brian Needham, Honorary School Historian, regarding various themes of the history of Oakham School, its pupils and teachers.

Two letters between Michael Yeld and the Headmaster Tony Little regarding the donation of a drawing of College House, made by Robert Norman Yeld when a pupil.

A headmaster's annual report for the academic year 1974-1975. Contents: Numbers; Staff; Academic; Faculty Reports; Chapel; Library; Drama; C.C.F., Scouts, Duke of Edinburgh Award Scheme; Health; The School Council; Old Oakhamians; The Oakham School Nursery Group; The International Club; Accommodation; General. Attached is a job description for a Public Relations Co-Ordinator and Conference Organiser (appendix A). Seven pages A to G.

A headmaster's annual report for the academic year 1966-1967. Contents: Numbers; Staff; Academic; Chapel; Drama; Societies; C.C.F.; Sport; Careers; Health; Accommodation; Nursery Group; Old Oakhamians; General. Twelve pages A to L.

A headmaster's annual report for the academic year 1968-1969. Contents: Numbers; Staff; Academic; Faculty Reports; Chapel; Library; Drama; Societies; C.C.F.; Health; Accommodation; Old Oakhamians; General. Ten pages A to J.

This collection highlights the depth and breadth of the school's curriculum and pupil's work. The drama and music sub-series are particularly detailed with their collection of production stills and programmes.

CUR/7 contains reports relating to the school's teaching and curriculum alongside timetables for lessons and exams, and comprehensive examination results for GCSE, A Level and IB.

Throughout the series in this collection, there is material relating to events and trips undertaken by various departments to increase the extra-curricular activities of pupils.

A letter from the Headmaster Richard Bull to John Barber regarding his arriving at Oakham School, and gratitude to staff and Old Oakhamians in his first term.

A letter from the Headmaster John Buchanan to Richard Walker regarding the current leadership at Oakham School and Richard's A-levels results.

A photograph of Mary Grimley, P.E. teacher, in 1994-1995.

A photograph of Sue Healey, Biology teacher, in 1994-1995.