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.

Guidelines on the Tutorial system at Oakham School, presented to a staff seminar on 24 June 1986 by the Headmaster, Graham Smallbone. The paper discusses safeguarding and pastoral issues that might be encountered and mentions what is expected of a tutor and how they should behave. The four pages are numbered A to D.

Guidelines for Middle School Tutors, detailing their general responsibilities and their pastoral role at Oakham School. Two pages numbered A and B.