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This file focusses on letters sent or received by William Spicer Wood, Headmaster, in the mid-19th century.

This series focusses on the headmastership of Rev William Spicer Wood (1846-1875) and contains items created by the headmaster himself as well as items relating to the life at School in the mid-19th century.

This file focusses on letters and cards relating to Oakham School, sent/received under the headmastership of Rev Vere Hodge.

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 letter from Colin Edgar to Dr Joe Spence, Headmaster, enclosing "The Humf Letters".
"The Humf Letters" is a work by Colin Edgar, compiling letters sent by Lt. Douglas Herbert Washington Humfrey to Betty Dawes from the front during the First World War.

The script of the short play "The Humf Letters", based on Colin and Anne Edgar's work compiling letters sent from the Western front by Douglas Humfrey to Betty Dawes. The play was written by Year 12 Drama A-level pupils of St Bartholomew's School, Newbury.

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.

Six letters between the Headmaster, John Buchanan and Rev Austin Boggis regarding the arrangements for a retreat and conference of Schoolmasters in the Holy Orders to be held at Oakham School in September 1961.

This sub-series contains letters to the C.C.F. and Shooting team. The whole collection of letters is relating to the School's success at Bisley in 1964.

This sub-file focusses on two letters bet the Headmaster, John Buchanan, and O.O. Alwyne John Westmoreland ('32) regarding Oakham School winning the Ashburton Shield in 1966.