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This series focusses on staff leavers, including list of staff changes, invitations to Leavers' events and booklets celebrating staff's time at Oakham School

A collection of reports and financial statements, and letters, related to the activities of Oakham School Enterprises Ltd (OSEL), spanning from 1978 to 1995.

An invitation from the Headmaster Graham Smallbone to local dignitaries to the launch of the Oakham '93 appeal, held in the QET on 17 April 1993.

A letter from Roger Blackmore to Peter Gravells, Executive Chairman at Catering by County Ltd, regarding the ox roast letter, the Grand Ball letter and OSEL's demands.

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 the Headmaster, John Buchanan, to Old Oakhamians regarding the upcoming reunion for the Talbot Griffith generation on 16 July 1972.

A letter (page A) from Graham Smallbone, Headmaster, and Rev Terence Treanor, Honorary Secretary of the Old Oakhamian Club, seeking to update Old Oakhamians' records and to launch the appeal for a new library; attached is a questionnaire (page B).

A letter from Headmaster G. Talbot Griffith to Old Oakhamians inviting them to lunch and tea on the occasion of the Old Oakhamian Quinquennial gathering on 29 July 1939.

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.