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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.

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 sub-file contains post cards related to the building and dedication of the War Memorial Chapel. Three post cards show the service of the laying of the foundation stone on Speech Day 1924. Four post cards show the dedication service on 29 October 1925. All post cards were published by Heawood & Son.

An almost complete collection of the School's magazines dating from 1884.

Oakham School Magazine, recording the Summer term 1902 (published in Winter term 1902). Contents: Editorial; School Notes; In Memoriam; Prize distribution and Speech Day; Letter from South Africa; Cricket. Nine double-pages A to I.

Oakham School Magazine, recording the Summer term 1901 (published in Winter term 1901). Contents: Editorial; School Notes; Speech Day; Football; Cricket. Seven double-pages A to G.

Oakham School Magazine, recording the Summer term 1899 (published in Winter term 1899). Contents: Editorial; School Notes; Speech Day; Cricket; Football; Correspondence.

Oakham School Magazine, recording the Summer term 1897 (published in Winter term 1897). Contents: Editorial; School Notes; Old Oakhamian Club; In Memoriam; Prize Day; Cricket; Correspondence. Nine double-pages A to I.

Oakham School Magazine, recording the Summer term 1892 (published in Winter term 1892). Contents: Speech Day; School Notes; The Magillicuddy Reeks; Pilography; A Corner of Paris; Poetry; Cricket; Correspondence. Nine double-pages A to I.

Oakham School Magazine, recording the Summer term 1891 (published in Winter term 1891). Contents: Editorial; School notes; Speech Day; The Brocken; Palmistry; Proverbs; Poetry; Old Oakhamian Club; Balance sheets; In Memoriam; Swimming Sports; Cricket; Correspondence. Nine double-pages A to I.