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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.

The Oakhamian Magazine, recording the Summer term 1971 (published in Winter term 1971). Contents: School News; Term's Eye View; Around the Societies; Drama; Music; Careers; Poetry; Travellers' Tales; Games; Avete; Valete.

This series focusses on the headmastership of Walter Lee Sargant (1902-1929) and contains items relating to the life at School in the early 20th century, its staff and pupils.

This sub-series focuses on letters related to the history of Wharflands house, its pupils and staff.

Old Oakhamian Calendar, published in 1930. Cover with contents: Frontispiece; Editorial; Names and Addresses of Members; Annual Dinners; Headmaster's Letter; Mr J. Story's Letter; Quinquennial Luncheon and Meeting; Resignation of Mr W.L. Sargant - An Appreciation; The Captain of the Ship; Presentation to Mr W.L. Sargant; Cambridge Letter; The Book of Oakham School and The Register; Births, Marriages and Deaths; Cricket, Football and Shooting Matches; The Golfing Society; Club Notices; School Staff. Eighteen double-pages A to R.

This series focuses on Wharflands pupils and staff since its opening in 1920. Most of the series is made of house photographs, various photographs of Housemasters and administration documents.