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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)

A prospectus for the school including staff list, trustees, the history of the school, information on the timetable, uniform, holidays, chapel, boarding, curriculum, Libraries, games, admission, scholarships, day boys and pocket money. Also includes clothes list, rules for the Old Oakhamian club, programme for speech day, admission form and note regarding photographs. Items A to O

This series focusses on the headmastership of Grosvenor Talbot Griffith (1935-1958) and contains items relating to the life at School in the mid-20th century, its staff and pupils.