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This series focusses on the headmastership of Tony Little (1996-2002) and contains items relating to the life at School in the 1990s and early 2000s, its staff and pupils.

A headmaster's annual report for the academic year 1984-1985. Contents: Some Thoughts on 1984/1985; Registrations/Entry Numbers; The Houses; Oakham Nursery School; Staff; General Academic; Examination Administration; University Entrance; Afternoon Activities; Sport Centre; Chapel; Food; Sanatorium; A.V.A. Centre; Careers Advice/ISCO Tests; Preparatory Schools Liaison/13+ Entry; Publicity/OSEL/Prospectus etc: The Queen Elizabeth Theatre; New Zealand Tour/Kenya Expedition; School Library; Old Oakhamian Club; House Names; Housemasters/Housemistresses; Conclusion. Attached are replies to a questionnaire for prospective parents (appendix A), some additional comments by Michael Stevens, a questionnaire for prospective parents, Overseas Universities Entries (appendix B), A-Level results (appendix C), O-Level results (appendix D), University entrance (Appendix F), a summary on Fastnet. Twenty-Seven pages A to AA.

A small red book containing staff list, school list and school calendar for the Winter term 1985. Item belonged to Mrs A. Frame, Accounts Clerk. It is the first Red Book of Graham Smallbone's headmastership.

A small red book containing staff list, school list and school calendar for the Spring term 1987; hand-written notations. Item belonged to Mrs J.E. Coleman.

A small red book containing staff list, school list and school calendar for the Winter term 1989; hand-written notations.

A small red book containing staff list, school list and school calendar for the Spring term 1990; hand-written notations and amendments. Item belonged to Mrs M. Frame.

A small red book containing staff list, school list and school calendar for the Spring term 1991.

A small red book containing staff list, school list and school calendar for the Summer term 1991; hand-written notations. Item belonged to Dr John Cheverton.

A small red book containing staff list, school list and school calendar for the Spring term 1992. Item belonged to Mrs J.E. Coleman.

A small red book containing staff list, school list and school calendar for the Summer term 1992. Item belonged to Dr John Cheverton.