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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.

Order of service for a memorial service for Walter Lee Sargant in the School Chapel on 22 September 1956.

Oakham School Magazine, recording the Summer term 1904 (published in Winter term 1904). Contents: Editorial; School Notes; Prize-Giving; Swimming Sports; Cricket.

Oakham School Magazine, recording the Summer term 1905 (published in Winter term 1905). Contents: Editorial; School Notes; Shooting Match; Swimming Sports; Death of Dr Ellicott; Speech Day; The Cricket Season. Seven double-pages A to G.

Oakham School Magazine, recording the Spring term 1906 (published in Summer term 1906). Contents: Editorial; School Notes; Oakham School Sixty Years Ago; The Sports; Cricket; Correspondence.

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 Summer term 1911 (published in Winter term 1911). Contents: School Notes; Speech Day; The Officers' Training Corps; Swimming Sports; Cricket. 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.

Oakham School Magazine, recording the Spring term 1912 (published in Summer term 1912). Contents: Editorial; School Notes; The Sports; The Debating Society; Easter Entertainment; Lake Como; The Great Plateau of Northern Rhodesia; Cricket Prospects for 1912. Seven double-pages A to G.

Oakham School Magazine, recording the Spring term 1913 (published in Summer term 1913). Contents: The New Buildings; School Notes; The Sports; The Debating Society; New Zealand; Montenegro as I saw it; Forest Life; Cricket Prospects for 1913; Football. Eight double-pages A to H.