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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.

A photograph of Father Douglass visiting the School in 1928. The photograph shows Father Douglass, Rev Scriven, Rev Edward Vere Hodge, Rev Frank Jerwood, Helen Hodge and Walter Lee Sargant in front of the Chapel.

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.

A letter (A) from Rev Austin Boggis to the Headmaster, John Buchanan, regarding organising the Chaplain's conference at Oakham School in 1961. Enclosed is a programme (B) for the 1960 Retreat and Conference of Schoolmasters in Holy Orders, held on 12-15 September at St Lawrence College, Ramsgate..

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

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.

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

This file focusses on letters sent/received by John Buchanan, chiefly during his headmastership (1958-1977).

This focusses on photographs of the Headmaster, Walter Lee Sargant, as well as various photographs of Oakham town in the early 20th century.