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A printed copy of "The Book of Oakham School" with register by Headmaster Walter Lee Sargant. Contents include a preface, the foundation and the early years of Oakham School, lists of Governors, Headmasters and Ushers, of Exhibitioners and two register s, 1836-1874 and 1971-1906.

A booklet giving advice to Upper School tutors on how to talk to their tutees about sex and relationships. Covers topics such as consent, rights, responsibilities, allegations of rape, STIs, contraception, facts and figures, sexting, pornography and indecent photographs.

A booklet for Form 3 pupils with various challenges inside which form part of wellbeing such as performing random acts of kindness, reading a book for pleasure and being screen-free for 24 hours.

A booklet aimed at Lower School tutors, detailing the tutorial programme of the year, containing various essential points to cover in First and Second forms, guidance on bullying, healthy eating, road safety, stranger danger, sex, smoking, alcohol, drugs, and listing reference videos and books.

A list of the 20 School Rules from 1965, organised into five sections: Bounds, Leaves, Dress, Transport and Miscellaneous. Two pages numbered A and B.

A sheet of paper with a list of Schools and names, possibly Senior Mistresses, and on the reverse, notes on working relationships and women in the workplace.

A draft programme for a H.M.C. Co-Educational Schools Meeting of Headmasters and Senior mistresses held at Reading on 08 March 1990.

Some notes written by Jane Matthews at a Senior Mistresses Conference (Midlands), including the programme of the day and a list of participants.

Information sheet on Social Behaviour and Discipline at Oakham School, containing three extracts from parents' letters.

A note written by Jane Matthews on what Graham Smallbone wanted to find out regarding how other co-educational schools choose their Resident Tutors.