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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 Spring term 1996. Contents: History; English; Performing Arts; C.C.F.; Science; Miscellany; Geography; Gap Year; Art; Sport; Houses; Miscellany.

The Oakhamian Magazine, recording the Summer term 1995. Contents: Farewells; English; Jerwoods in Paris; Science; Music; Performing Arts; Miscellany & Gap Years; Art & Design; Activities; Sport; Miscellany & Houses.

The Oakhamian Magazine, recording the Summer term 1994. Contents: Speech Day & Places '94; Farewells & Places '93; English; Languages; Houses; Travel & Adventure; Performing Arts; DofE Canoeing; Art & Design; Sports; Miscellany & Editorial.

A letter from David Smith and Ian Robson to the Headmaster Graham Smallbone regarding the refurbishment of Old School.

A bound copy of several Oakhamian Magazines from Summer 1993 to Summer 1997.

Four photographs of five people posing in front of the new Peter Collins organ in the School Chapel. They are (L to R): Peter Collins (Builder), David Woodcock (Head of Music), Peter Hurford (Organist), Graham Smallbone (Headmaster) and Simon Schanschieff (Chairman of the Trustees). The photographs are all slightly different (A to D).

A programme for the inaugural recital by Peter Hurford on 26 June 1993 and the Service of Dedication by the Right Reverend William Westwood on 27 June 1993, including a brief history of the organs of Oakham School Chapel, a biography of Peter Hurford, and a description of the new Peter Collins organ.

A letter from the Headmaster Graham Smallbone to peter Collins, Organ builder, regarding the carvings, which are a gift from the Whites, and the open day and the Derbyshire Organist Association.

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.