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A headmaster's annual report for the academic year 1980-1981. Contents: Registrations/Entry; The Upper and Middle School Houses; Jerwoods; Discipline; Staff; General Academic; The Departments; A-Level and O-Level; University Entrance; The Library; Drama; P.E. and Sport; Sports Centre; Chapel; Voluntary Service; C.C.F.; Duke of Edinburgh Award Scheme; Exploration Society; Sea Scouts and Guides; Senior Societies and Middle School Societies; Careers; Publicity and Local Relations; Audio-Visual Aids Centre; The Oakhamian; The Ashburton Hall; School Council; Sanatorium; Old Oakhamian Club; Oakham School Nursery; Postscript. Seventeen pages A to Q.

A headmaster's annual report for the academic year 1978-1979. Contents: Numbers; Academic; Careers; A.V.A. Centre; Library; Art & Design; Music; Physical Education; Sports Hall; Playing Fields; Shooting; Drama; C.C.F.; The Duke of Edinburgh's Award Scheme; Exploration Society; Scouts & Guides; Discipline and the Decem; The Houses; The Chaplaincy; Ashburton Hall; School Council; The Oakhamian; Senior and Middle School Societies; Voluntary Services; The Sanatorium; Oakham School Nursery; Old Oakhamian Club; Conclusion. Attached are A-Levels results (appendix A), O-Level results (appendix B), Summary of University applications and places gained (appendix C), a memorandum on Development of the Sargant Laboratories and a final report on Svalbard '79. Twenty-one pages A to U.

A photograph of Dermot Gilvary watching a cricket match. Date is unknown.

A photograph of Dermot Gilvary, probably in 1997.

A photograph of Dermot Gilvary in 1994-1995.

A letter from the Headmaster Graham Smallbone to Dermot Gilvary, Head of Drama, regarding some décor being nailed to the woodwork in the Shakespeare Centre and proper use of the building.

A bound copy of several Oakhamian Magazines from Summer 1993 to Summer 1997.

The Oakhamian Magazine, recording the Spring term 1994. Contents: Arts; Houses; Medicine; Languages; Art & Design; Sport; Sports Results; Miscellany.

The Oakhamian Magazine, recording the Summer term 1996. Contents: Farewells; History; Science; Miscellany; English; Languages; Art; Performing Arts; Sport; Houses; Miscellany.

A bound copy of several Oakhamian Magazines from Winter 2002 to Winter 2004.