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This sub-series contains books used by pupils during services in chapel or books published by staff or Old Oakhamians and given to the school. A large part of this sub-series contains hymns books compiled by Rev T.C.H. Clare ('29).

A prospectus promoting studying at Oakham School in 1943. Contents: Trustees & Staff; Foundation & History; The School today; Situation & Surroundings; Premises & Equipment; School Terms, Holidays, Timetable; Chapel Services, Religious Instruction; Curriculum; Libraries; Reports; Boarding Houses; School House, Wharflands, The Junior House; Clothes; Diet & Tuck Boxes; Health; Absence & Leave; Games; Physical Education; J.T.C.; Scouts; Activities outside the classroom; Entry, Fees, Remission of Fees for absence; Optional Payments, Extras; Pocket Money; Scholarships; Leaving Scholarships; Notice of leaving; Expenses; Appointments with the Headmaster; Day Boys; Publications; Old Oakhamian Club. Six double-pages A to F. Enclosed is a list of Trustees and Staff (G).

A prospectus promoting studying at Oakham School in 1942. Contents: Trustees & Staff; Foundation & History; The School today; Situation & Surroundings; Premises & Equipment; School Terms, Holidays, Timetable; Chapel Services, Religious Instruction; Curriculum; Libraries; Reports; Boarding Houses; School House, Wharflands, The Junior House; Clothes; Diet & Tuck Boxes; Health; Absence & Leave; Games; Physical Education; O.T.C.; Scouts; Activities outside the classroom; Entry, Fees, Remission of Fees for absence; Optional Payments, Extras; Pocket Money; Scholarships; Leaving Scholarships; Notice of leaving; Expenses; Appointments with the Headmaster; Day Boys; Publications; Old Oakhamian Club. Nine double-pages A to I. Enclosed is modifications to the clothes list due to Rationing in July 1941 (J).

This file focusses on admission prospectuses published throughout G. Talbot Griffith's headmastership.

Four letters, collated on one A3 sheet, addressed to the Headmaster Tony Little and Charles Welch, to thank them for various events such as the Harvest Party in 1997 and Oakham School's contribution to the Andrew Martin Trust.

This series focusses on documents relating to Brian Welford' career at Oakham School as Master-in-charge of Rugby in the 1970s and 1980s. Also contains documents relating to the history of rugby and Old Oakhamians, kept by Mr Welford in his personal files.

This series focusses on obituaries, tributes and memorial services in memory of staff, teachers and their family.

Newspaper cuttings printed on one page reporting on the 1979 rugby visit from Japan School to Oakham School.

This file focusses on various documents relating to Sports at Oakham School.

A collection of documents relating to Round House, the first purpose-built girls’ boarding house, built in 1972 on what was School House tennis court. The Architect, Tom E. Wilson, designed a building in the shape of a Dovecote, or a Birdcage. The builders were George Duxbury (OO, '34) and Sons. The new house contained thirty bed-sitters on three floors, built around a central spiral stairway. A common room linked the new building with the War Memorial Library. At the back of the Library were built a small flat and domestic offices. Sixty girls moved in from the beginning of the 1972 Winter term and the boarding house was officially opened on 28 October 1972 by Mrs Haywood.