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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.

A School list of staff and pupils for the Summer term 1903. Contents: Trustees; Teachers; Forms VI to I; Successes since Midsummer, 1902; Oxford & Cambridge Board, 1903; Royal Drawing Society. Five double-pages A to E.

A prospectus promoting studying at Oakham School in 1902. Contents: Trustees & Staff; Subjects; Upper School & Lower School; Examinations; Boarding Houses; Library, Games & Extras; Terms; Holidays; Infectious Disease; Scholarships, Exhibitions & Prizes. Three double-pages A to C.

This file focusses on various prospectuses published under the headmastership of Walter Lee Sargant in the early 20th century.

A prospectus promoting studying at Oakham School in 1903, with illustrations. Contents: Brief History; Subjects of Instruction; Boarding Houses; Health; Games; Holidays.