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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.

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 roll call for School House, Mr. Scriven's, Mr Williams', Bank House and the Day Boys in Winter term 1887. One name has been hand-written in Form VI.

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.

Oakham School Magazine, recording the Winter term 1909 (published in Spring term 1910). Contents: Editorial; School Notes; The Concert; Lectures; The Old School Frescoes; "Rondeau"; Football; Balance Sheet - Games Fund - 1909. Seven double-pages A to G.

Oakham School Magazine, recording the Winter term 1911 (published in Spring term 1912). Contents: School Notes; The Concert; Mr. F.H. Shera's Pianoforte Quintet; Lectures; Football; Balance Sheet - Games Fund, 1911. Seven double-pages A to G.

Issue no. 5 of "The Old Oakhamian". Contents: Annual Dinner, Old Oakhamian Fund, Cricket, Football and Golf, School Notes, Births, Deaths and Marriages, O.O. Notes, New Members, Changes of Address, Notices, School Football Fixtures, Correspondence.

A bound copy of several Oakhamian Magazines from 1932 to 1936.

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 prospectus promoting studying at Oakham School c.1909, with illustrations. Contents: Trustees & Staff; Brief History of the School; Subjects of Instruction; Upper School & Lower School; Boarding Houses; Health; Games; Holidays; Term's fees Scholarships and Exhibitions.