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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.

The Oakhamian Magazine, recording the Summer term 1941 (published in Winter term 1941). Contents: Roll of Honour; School News; Frank Emerson Chapman; Music Notes; J.T.C.; A.T.C.; Scout Notes; Swimming Sports; Football; Correspondence; O.O. Notes. Six double-pages A to F.

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.