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A photographic album of the school (but mainly of Wharflands house) from the Talbot-Griffiths era. Photographs of various staff members, buildings, House prefects, scouts, sporting photos (steeplechase, water-polo, rugby), House photos (Wharflands), Drama photos (Midsummer's Nights Dream and Macbeth 1953), The 1953 Elizabethan Fair, Form 4A photo (1951 and 1953), The choir, the Memorial Library opening, a christening, the visit to RCAF N.Luffenham Swindells, and the proclamation of Queen Elizabeth II.

All the items in this series are related to the frescoes in Old School, commissioned by Walter Lee Sargant and painted by his sister, Mary Sargant-Florence, illustrating the "Story of Gareth".

A group of photographs of the interior of Old School, including some of the frescoes, and a letter regarding Mary Sargant Florence's life and work.

A black and white photograph of the interior of the Old School and the frescoes, probably published in the Oakhamian Magazine.

A short history of the commission of the frescoes and the "Story of Gareth", inspiration for the paintings in Old School, including the sketches of the frescoes. Five pages A to E.

The items in this series are related to Pastoral Care at Oakham School. Various topics include wellbeing, resources for tutorial, discipline and school rules, child protection and staff training.

A4 poster for the Anti-Bullying Awareness Day on Friday 20 November at Oakham School, with the support of BullyingUK.

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

Oakham School's Drugs policy.