A letter from the Headmaster Graham Smallbone to Parents regarding a review of the Summer term 1995, including the opening of the Library, the cricket season, the School inspection, exam results, fees, the Carol service and changes of staff.

A letter (A) from Graham Smallbone, Headmaster, Simon Schanschieff, Chairman of Trustees, and Rev Terence Treanor, Honorary Secretary of the Old Oakhamian Club, to former pupils who were at Oakham during John Barber's years with the School regarding celebrating his eightieth birthday and the Barber Archives. Attached is a reply slip (B).

A letter from J.D. Buchanan, former Headmaster, to Old Oakhamians asking their support to finance the Information and Study Centre, as part of the 1993 Development Plan. Two pages A and B.

A letter from The Right Honourable the Lord Chalfont to the Headmaster Graham Smallbone regarding sending a copy of 'This War called Peace' to the School Library.

A letter from the Headmaster Nigel Lashbrook to Parents at the end of the Winter term 2018. Contents: Parent/Teacher Committee; Teaching & Learning; Website and School Portals; Sustainability.

A letter from Rt Hon William Hague MP to the Headmaster Tony Little, thanking him for the visit of the school and the opening of the Day houses.

A book bill for Midsummer 1840 on A.F. Padley's account; listing titles and their fees.

Notes by the Headmaster Graham Smallbone on the future needs of the School for a discussion in January 1986. Two pages A and B.

A headmaster's annual report for the academic year 1960-1961. Contents: Numbers; Staff; Activities; Health; Accommodation; General Remarks. Attached is a general planning review (appendix A). Eleven pages A to K.

A headmaster's annual report for the academic year 1966-1967. Contents: Numbers; Staff; Academic; Chapel; Drama; Societies; C.C.F.; Sport; Careers; Health; Accommodation; Nursery Group; Old Oakhamians; General. Twelve pages A to L.