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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.

A School list of staff and pupils for the Spring term 1887. Contents: Staff; Upper Vi to Form I; Special prizes and Distinctions since last term.

Oakham School Magazine, recording the Summer term 1902 (published in Winter term 1902). Contents: Editorial; School Notes; In Memoriam; Prize distribution and Speech Day; Letter from South Africa; Cricket. Nine double-pages A to I.

Oakham School Magazine, recording the Summer term 1901 (published in Winter term 1901). Contents: Editorial; School Notes; Speech Day; Football; Cricket. Seven double-pages A to G.

Oakham School Magazine, recording the Summer term 1897 (published in Winter term 1897). Contents: Editorial; School Notes; Old Oakhamian Club; In Memoriam; Prize Day; Cricket; Correspondence. Nine double-pages A to I.

Oakham School Magazine, recording the Winter term 1894 (published in Spring term 1895). Contents: Frontispiece; Editorial; School Notes; The Concerts; In Memoriam; The Gymnasium; Some Experiences of the Slums of London; Football; Correspondence. The first page is a photograph of the Rugby 1st XV 1894-1895. Eight double-pages A to H.

Oakham School Magazine, recording the Winter term 1891 (published in Spring term 1892). Contents: The Concerts; School Notes; Old Oakhamian Club; Skating in the Fens; Analogies of Thought; Poetry; Proverbs; In Memoriam; Balance sheet (Library); Football; Correspondence. Nine double-pages A to I.

Oakham School Magazine, recording the Summer term 1893 (published in Winter term 1893). Contents: Editorial; School Notes; Marriages; The Ancient Home of the Hattons; On the Broads; Tits; Dominica; Cricket.