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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 focusses on photographs of the Headmaster, Walter Lee Sargant, as well as various photographs of Oakham town in the early 20th century.

A collection of photos of Tom Sargant including Sargant with Black, Sargant with C.J.B.Scriven, E.V.Hodge, Father Douglass, F.H.Jerwood, Mrs Hodge, and Mrs Sargant (scan 00721), (scan 00337, 00347, 00662), (scan 00341)

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.