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Order of service (A) for the memorial service celebrating the life of John David Buchanan, held in Chapel on 30 September 2005. Enclosed are a donation slip to a Memorial Bursary (B) and a blank tribute card (C).

A CD of photographs of a cricket match between Marylebone Cricket Club and Old Oakhamians in 2014.

Two letters (A and B) from Graham Smallbone, Headmaster, and John Buchanan and Rev Terence Treanor asking Old Oakhamians to support the construction of the new library as part of the 1993 Development Plan. One letter was sent to O.O. who left in 1965 or earlier; one letter was sent to O.O. who left in 1966 or later.

Order of service for the marriage of Kim Mortimer and Jon Wills, P.E. teachers, in the School Chapel on 23 July 1983.

Order of service for a service following the inauguration of the High Sheriff of Rutland, Peter Lawson, in the School Chapel on 8 April 2011.

A poster advertising an online meeting with Old Oakhamians discussing Science careers. The meeting took place online over lockdown in Summer term 2020.

A poster advertising an Oakham School Medical Society event with Old Oakhamians discussing Medicine careers held in the Wilson Auditorium on 23 March 2022.

A headmaster's annual report for the academic year 1974-1975. Contents: Numbers; Staff; Academic; Faculty Reports; Chapel; Library; Drama; C.C.F., Scouts, Duke of Edinburgh Award Scheme; Health; The School Council; Old Oakhamians; The Oakham School Nursery Group; The International Club; Accommodation; General. Attached is a job description for a Public Relations Co-Ordinator and Conference Organiser (appendix A). Seven pages A to G.

A headmaster's annual report for the academic year 1973-1974. Contents: Numbers; Staff; Academic; Faculty Reports; Chapel; Library; C.C.F., Scouts, Duke of Edinburgh Award Scheme; Health; Accommodation; Old Oakhamians; Nursery School; General. Attached are a report on a teaching exchange in the US (appendix A), and a report on the Nursery Group (appendix B). Six pages A to F.

A headmaster's annual report for the academic year 1972-1973. Contents: Numbers; Staff; Academic; Faculty Reports; Chapel; Library; Drama; C.C.F., Scouts, Duke of Edinburgh Award Scheme; Health; Accommodation; Old Oakhamians; Oakham School Nursery Group; General. Attached are a report on a teaching exchange in the US (appendix A), and a report on the Nursery Group (appendix B). Eight pages A to H.