Order of service of the service of thanksgiving for the life of Dr John Cheverton held at the School Chapel on 25 March 2011.

Order of service of the service of thanksgiving for Auriol Chandler held at the School Chapel on 2 June 2015.

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).

This series is related to the charity work at Oakham School, including the fund raising and other events organised at school by staff, pupils, houses and the Oakham School Charities Association (OSCA) in aid of various charities and the local community.

A prospectus (A) promoting studying at Oakham School in 1935. Contents: Trustees; Staff; Admission; Work; Fees; Optional Payments; Absence & Remission of Fees; Health; Entrance Scholarships; Other Scholarships & Exhibitions; Buildings; Boarding Houses; Holidays & Hours; Games & Hobbies; School Societies; Expenses; Clothes List. Enclosed are corrections to prospectus (B), and a form of application for admission (C).

Part of a prospectus promoting studying at Oakham School in 1929. Contents: Trustees & Staff; Brief History of the School.

A document written by Pam Baillie, Senior Mistress of Pocklington School, discussing the different attitudes to girls' sports in co-educational schools, staffing needed, facilities, and some solutions to foreseen issues. Three pages numbered A to C.

A blank form which encourages people to think about how they can make improvements.

A series of letters and documents related to Dr Thomas Orme, Headmaster of Oakham School between 1778 and 1796.

Several documents containing a list of staff walking, driving, marshalling or manning the checkpoints, with emergency contacts and information for staff on safety and the route. Eleven pages A to K.