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A letter from the Headmaster Graham Smallbone to Parents regarding a review of the Winter term 1985. Contents: Reports; Scholars; Examinations; Appointments; School accounts; Insurance; Music fees; Activity holidays; Games; Chad '86 Appeal and OSCA. Two pages A and B.

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 Graham Smallbone to Parents reviewing the Winter term 1992. Contents: The Future; Examination fees; Choral Society performance; Rutland - A Visitor's Guide; Three Special Requests; Responsibility for each other. Two pages A and B.

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 from the Headmaster Graham Smallbone to Parents regarding a review of the Spring term 1996. Contents: Drugs guideline; Events of the term; the Hospital Site.

A letter from the Headmaster Graham Smallbone to R.T. Constable-Maxwell, High Sheriff of Leicestershire, regarding the Court Opening in Oakham and providing the choir.

A letter from the Headmaster Graham Smallbone to Mrs Vera Furner regarding the donation of Mr Maurice Kingham's Autigraph book.

A letter from former teacher Greg Andrews to the Headmaster Nigel Lashbrook regarding his time at Oakham School (A), and enclosing a letter from John Buchanan (B).

A letter from the Headmaster Designate Henry Price to Parents announcing the appointment of Dr Leo Dudin as Deputy Head Academic in June 2018.

A letter from the Headmaster Designate Henry Price to Parents announcing the appointment of Arthur Mayhew as Senior Deputy Head in November 2018.