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This series focusses on the headmastership of Rev Edward Vere Hodge (1879-1902) and contains items relating to the life at School in the late19th century, its staff and pupils. The series contains some of the earliest photographs of Oakham School's collection.

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 1888 (published in Winter term 1888). Contents: The Speech Day; Organ recital; The Italian Exhibition; Bound for Australia; Handel; Old Oakhamian Club; Poetry; Cricket; School Notes. Eleven double-pages A to K.

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 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 1904 (published in Winter term 1904). Contents: Editorial; School Notes; Prize-Giving; Swimming Sports; Cricket.

Oakham School Magazine, recording the Summer term 1905 (published in Winter term 1905). Contents: Editorial; School Notes; Shooting Match; Swimming Sports; Death of Dr Ellicott; Speech Day; The Cricket Season. Seven double-pages A to G.

Oakham School Magazine, recording the Summer term 1911 (published in Winter term 1911). Contents: School Notes; Speech Day; The Officers' Training Corps; Swimming Sports; Cricket. Seven double-pages A to G.

Oakham School Magazine, recording the Summer term 1913 (published in Winter term 1913). Contents: School Notes; Swimming Sports; The Officers' Training Corps; Speech Day; Cricket; Football Prospects for 1913. Seven double-pages A to G.

Oakham School Magazine, recording the Summer term 1920 (published in Winter term 1920). Contents: School Notes; Speech Day; The Cricket Season; Lectures. Five double-pages A to E.