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

A bound copy of several Oakhamian Magazines from February 1988 to February 1991.

The Oakhamian Magazine, recording the Winter term 1980 (published in February 1990). Contents: Editorial; People - Places - Events; OSCA; Travel; Music; Drama; Talkback; Sport.

The Oakhamian Magazine, recording the Summer term 1992 (published in October 1992). Contents: People - Places - Events; Drama;General; Tanzania Expedition; Houses; Speech Day; Music; Valedictory; Sport.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Summer term 2019. Contents: Feature; Academic; Performing Arts; Trips and Tours; Pastoral; Cover Story; Activities; Sport; Staff News; Beyond Oakham; Old Oakhamian.

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.

The Oakhamian Magazine, recording the Summer term 1997. Contents: Farewells; Jerwoods Activities; Languages; Science; Art; Sport; Geography; Miscellany; Performing Arts; Houses; Miscellany.

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

This sub-series focuses on the history of the 1993 Organ in the School Chapel. After the 1930 organ expired and was replaced by a computer organ in the 1980s, the headmaster Graham Smallbone commissioned for a new organ to be built. Some items highlight the various proposals, the correspondence focuses on the building and installation of the organ and the photographic file finally shows the organ in Chapel.