- 1989/1990: Michael Bogdanov – The Wars of the Roses
- Richard Eyre – Racing Demon and The Voysey Inheritance
- Nicholas Hytner – Ghetto and Miss Saigon
- Trevor Nunn – Othello
- 1991–1995: see Best Director of a Play and Best Director of a Musical
- 1996: Sam Mendes – Company and The Glass Menagerie
- Richard Eyre – Skylight and La Grande Magia
- Adrian Noble – A Midsummer Night's Dream
- Matthew Warchus – Volpone and Henry V
- 1997: Des McAnuff – Tommy
- Richard Eyre – John Gabriel Borkman
- Anthony Page – A Doll's House
- Matthew Warchus – 'Art'
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- 1998: Richard Eyre – King Lear
- Walter Bobbie – Chicago
- Sam Mendes – Othello
- Matthew Warchus – Hamlet
- 1999: Howard Davies – The Iceman Cometh
- Sam Mendes – The Blue Room
- Trevor Nunn – Oklahoma!
- Ian Rickson – The Weir
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