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A headmaster's annual report for the academic year 1985-1986. Contents: The School Year; Second Master's Report; Registrar's Report; Registrations/Entry Numbers; Director of Studies' Report; Scholarship Report; Christopher Dixon Prize; University Entries; A- and O-Level results; The Departments; Prep Schools Liaison Report; The Houses; Examination Administration; Drama and the Theatre; Careers; The Chaplaincy; A.V.A. Centre; Ashburton Hall; The Sanatorium; Library; The School Council; The Oakhamian; Old Oakhamian Club; Nursery School; Playing Fields; The Sports Centre; Afternoon Activities and Societies; Exploration Society; The Teaching Staff; OSEL/Public relations/Appeals; Conclusion. Attached are A-Level results (appendix C), O-Level results, Scholarship Awards (appendix A), Bursaries, University Entries (appendix B). Thirty pages A to AD.

A certificate awarded to Gunthorpe House for winning the OSCA house shield or banner competition, judged by Jenny Little and Reverend John Darrall in 1998.

A programme for the Jerwoods Sports Day on 30 June 1999, including a list of events, the house teams, the 1998 results, the rules of competition and a list of the officials. Three double-pages A to C.

A note with list of guests, staff and parents, attending the Third Form Parents' Evening at The Finches.

Order of service of the Service of Thanksgiving for Mary Stevens held at the School Chapel on 3 October 2023.

A print out of Oakham School Nursery staff at a leavers tea hosted by Mr & Mrs Little in Deanscroft on 28 June 2001, with list of names at the back.

The Old Oakhamian Magazine, published in Autumn 2002. Contents: Letter from the Editors; Dr joe Spence - Headmaster; '87 Reunion; Tony Little; O.O. Families' Day; Louise Doughty; The First One; Births, Marriages & Deaths; Three OOs in a Boat; Stars, Stripes and OOs; All Our Yesterdays; Obituaries; News of; Sport.

A balance sheet detailing the funds raised by each house during the year 1991-1992.

A report from Rev John Darrall to be published in the Oakhamian Magazine on the charity events organised during the Winter term 1989, including houses charity events, a Non-Uniform Day, and other sponsored events.

A report from Rev John Darrall to be published in the Oakhamian Magazine on the charity events organised during the year 1991-1992, including the Rutland Water Walk, a hunger lunch, concerts, and houses events.