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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 file focusses on roll call lists from the late 19th century/early 20th century, under the headmastership of Rev Edward Vere Hodge.

This file focusses on various items published under the headmastership of Rev Edward Vere Hodge in the late 19th century.

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.

This file focusses on roll call lists from the early 20th century, under the headmastership of Walter Lee Sargant.

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

Old Oakhamian Calendar, published in 1910. Cover with contents: Editorial; Members of the Old Oakhamian Club - 1910; Old Oakhamian Notes; Old Boys' Matches; O.O. Club Accounts. Seven double-pages A to G.

A School list of staff and pupils for the Summer term 1902. Contents: Trustees; Teachers; Forms VI to I; Successes since Midsummer, 1901; Oxford & Cambridge Board, 1902; Royal Drawing Society. Five double-pages A to E.

A prospectus promoting studying at Oakham School in 1897. 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.

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.