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This file focusses on letter sent by Dr John Doncaster, Headmaster of Oakham School, regarding some pupils and staff matters. File dates from the first half of the 19th century.

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

A modern transcript of a letter from William Spicer Wood, Headmaster of Oakham School, and Edward Thring, Headmaster of Uppingham School, addressed to the Governors of both schools regarding the relation between schools and their future as separate institutions.

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 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.

Two letters (B and C) from Rev R.C.O. Goodchild to A.T.H. Starkey regarding salary earned and income tax in 1942; a reply (A) from A.T.H. Starkey to Rev R.C.O. Goodchild.

A letter from the Headmaster G. Talbot Griffiths to teaching staff regarding the renaming of the forms in the School from Easter term 1956.

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, John Buchanan, to Parents regarding the events of the Spring term 1958, including the hockey season, the works on the Sargant Laboratories, the raising of the minimum age of boarding and Speech Day. Two pages A and B.

A letter from the Headmaster, John Buchanan, to Rev Austin Boggis regarding possible dates for the 1961 Retreat and Conference of Schoolmasters in the Holy Orders to be held at Oakham School.