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This series focusses on the headmastership of Grosvenor Talbot Griffith (1935-1958) and contains items relating to the life at School in the mid-20th century, its staff and pupils.

A calendar of events in the Winter term 1935.

A prospectus promoting studying at Oakham School in 1922. Contents: Trustees & Staff; Brief History of the School; Subjects of Instructions; Boarding Houses; Buildings; Scale of Fees; Health; Scholarships and Exhibitions.

An inventory an valuation of furniture, fixtures and effects in and upon the premises known as 'Junior House', made for transfer from E. Pickering Clarke to the Trustees. Contains information on the building, its fixtures and fittings, in the dining room, kitchen, garden, toilets, pantry, sick room, matron room, dormitory, study, classroom, bathrooms, coal house, workshop, tool shed, gardens and tennis nets. Thirty-three pages A to AG.

This sub-series focuses on the administration and everyday running of the Junior House/Chapmans.