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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 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 letter from the Headmaster Richard Bull to Michael Stevens, Patrick Wilson and Housemasters regarding recommendations for the Anderson Awards.

A photograph of Dorothea Smallbone at an event, probably Speech Day.

This file focusses on photographs of Tony Little, during his Headmastership (1996-2002).

A letter from the Headmaster Designate Henry Price to Parents regarding Sports Day and Speech Day in Summer term 2021.

Oakham School Magazine, recording the Summer term 1886 (published in Winter term 1886). Contents: Speech Day; Bimetallism; Warwick Hall; Tit for Tat; Souvenirs de Genève; Bibliotheca Oakhamiensis; Sir Edward Buck; Lancashire; Poetry; Cricket; Correspondence;, School Notes. Nine double-pages A to I.

Oakham School Magazine, recording the Summer term 1888 (published in Winter term 1888). Contents: The Speech Day; Organ recital; The Italian Exhibition; Bound for Australia; Handel; Old Oakhamian Club; Poetry; Cricket; School Notes. Eleven double-pages A to K.

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