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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.

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.