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This series focuses on the boarding boys in Deanscroft, since its opening in 1948. The Headmaster himself was Housemaster, until 1971. Deanscroft boarding house was closed on Speech Day 1989, prior to its conversion into Stevens, a boarding house for girls. The boarding boys were moved to the newly built Haywoods House on Kilburn Road. The items include the complete set of house photographs and informal photographs showing boys around the house and on campus, as well as duty records.

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 (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.

A letter from Rev Austin Boggis to the headmaster, John Buchanan, regarding the arrangements for his retreat and conference at School in September 1961.

A letter A) from the Headmaster, John Buchanan, to Rev A.T.I. Boggis regarding a retreat and conference in September 1961. Enclosed is a suggested draft for the arrangements (B).

A letter from O.O. Alwyne Westmoreland to the Headmaster, John Buchanan, regarding Oakham School winning the Ashburton Shield, captained by Chris Frame, in 1966.

A letter from the Headmaster, John Buchanan, to O.O. Alwyne Westmoreland regarding Oakham School winning the Ashburton Shield in 1966.