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A headmaster's annual report for the academic year 1969-1970. Contents: Numbers; Staff; Academic; Faculty Reports; Chapel; Library; Drama; Societies; C.C.F., Scouts, Duke of Edinburgh Award Scheme; Health; Accommodation; The School Shop; Old Oakhamians; Second Development Campaign; General. Attached are university entrants list (appendix A) and a report on paying for private schools (appendix B). Fifteen pages A to O.

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.

A headmaster's annual report for the academic year 1967-1968. Contents: Numbers; Staff; Academic; Faculty Reports; Chapel; Library; Drama; Societies; C.C.F.; Health; Accommodation; Old Oakhamians; General. Attached is the Ruddles House report (appendix A). Eighteen pages A to R.

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 1965-1966. Contents: Numbers; Staff; Activities; Health; Accommodation; Old Oakhamians; Circular 10/65; General. Attached are A-Level results (appendix A) and a report on conference 'Life in Industry' (appendix B). Thirteen pages A to M.

Seven letters regarding the opening of the Rutland Crown Court in Oakham Castle on 13 January 1992.

Three letters between the Headmaster Graham Smallbone and Mrs Vera Furner regarding the donation of O.O. Maurice Kingham's autograph book to the School in 1995.

Two letters between the Headmaster Tony Little and Rosemary Goddard, sister of Geoffrey Brittlebank who dies in the Second World War, regarding visiting the War Memeorial.

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.

Three letters between Eileen Buxton and the Headmaster Tony Little regarding the death of Robert Henry Buxton, and the donation of his Oakham School crest to the School in 2001.