A letter from Elizabeth Cairncross, Senior Mistress of Christ's Hospital, to Jane Matthews regarding two items on the agenda for the Meeting at Lincoln College and enclosing the minutes of the H.M.C. Co-Educational Schools' Senior Mistresses Meeting held at Oakham School on 10 November 1988 and a list of the Senior Mistresses who attended the meeting. Three pages numbered A to C.

A letter from the Headmaster Graham Smallbone to Parents regarding a review of the Spring term 1986. Contents: Oxbridge Results; Summer Exeat and Parent/Teacher evening for Fourth Form; The Tutorial System; School House; School Uniform; Car Parking; OSCA; Remedial Teaching; School video, Parents' leaflet etc; Telex; Smoking.

A letter from the Headmaster Tony Little to Parents regarding the responses of a questionnaire sent to parents in 1997. Two pages A and B.

This sub-series relates to the history of the Cadets at Oakham School since 1910. The bulk of the collection is made of photographs of inspection throughout the 20th century.

A letter from the Headmaster Richard Bull to Parents regarding the Creative Arts in the Lower and Middle School, the influenza vaccination, the use Tippex and rules on Clothing.

A letter from the Headmaster Richard Bull to Parents regarding the dress code for the School photograph, the 1984 Ball and the new Activity Holidays brochure.

This series relates to Junior Boarding girls of Lincoln House. The house was built in 1974, as part of the new Jerwoods Campus for the Lower School. Most of the collection is made of the House photographs, as well as informal photograph of the girls in house events and sports competition, and programmes of some house events.

This sub-series focuses on the everyday running of Lincoln House. It contains reviews of the terms and the girls' achievements, as well as house lists an address lists.

A letter from the Headmaster Richard Bull to Parents regarding the Commemoration service, the Oakham School Young Masters, dressing code for School Photographs, the Quatercentenary Programme, the 1984 Appeal Raffle, the rule on tracksuits and second-hand uniform shop and guidelines on parties.

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.