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This series is related to the buildings on the School campus and documents their history. Most of the collection is made of photographs and artwork, as well as architectural plans. Each sub-series focusses on a different building.

Seven letters regarding the opening of the Rutland Crown Court in Oakham Castle on 13 January 1992.

This file focusses on letters received/sent by the Headmaster Graham Smallbone during his headmastership (1985-1996).

This series focusses on the headmastership of Tony Little (1996-2002) and contains items relating to the life at School in the 1990s and early 2000s, its staff and pupils.

The Oakhamian Magazine, recording the Summer and Winter terms 1987 (published in February 1988). Contents: Editorial; People - Places - Events; J. Walton; The Chapel; Poem - Consideration; Speech Day; Into Industry; OSCA; Being New; Denis Giuseppi; The Ashburton; The Barraclough Opening; Kenya; Drama; Poems; Sport; The Tramp; The Oxbridge Lie; Music; Societies and Travel; 20 years ago.

The Oakhamian Magazine, recording the Spring term 1988 (published in May 1988). Contents: Editorial; People - Places - Events; An Education Survey; Community Services; Drama; No Time to Stand and Stare; Music; The Line; Fourth Year Visit to Paris; Interview with the Headmaster; Poems; Art; Sport; Societies; Jerwoods Disco; Leavers' Destinations '87; Oxbridge Successes '87.

The Oakhamian Magazine, recording the Spring term 1989 (published in May 1989). Contents: Editorial; People - Places - Events; OSCA; Travel; Nostalgia; Societies; Music; Drama; Sport.

The Oakhamian Magazine, recording the Spring term 1991 (published in May 1991). Contents: People - Places - Events; OSCA; Societies; Lectures; Drama; Project Trust; Travel; Music; Lenten Address; Sport.

The Oakhamian Magazine, recording the Winter term 1992 (published in February 1993). Contents: People - Places - Events; Drama; General; Houses; Music; Cate's China; Phil's Japan; Sport.

The Oakhamian Magazine, recording the Spring term 1995. Contents: DofE; Music; English; Drama; Languages; Science; Girls Sport; Sport; Boys Sport; Miscellany; Houses; Art & Design.