- 2000: Michael Blakemore – Copenhagen
- James Lapine – Dirty Blonde
- David Leveaux – The Real Thing
- Matthew Warchus – True West
- 2001: Daniel J. Sullivan – Proof
- Marion McClinton – King Hedley II
- Ian McElhinney – Stones in His Pockets
- Jack O'Brien – The Invention of Love
- 2002: Mary Zimmerman – Metamorphoses
- Howard Davies – Private Lives
- Richard Eyre – The Crucible
- Daniel J. Sullivan – Morning's at Seven
- 2003: Joe Mantello – Take Me Out
- Laurence Boswell – A Day in the Death of Joe Egg
- Robert Falls – Long Day's Journey Into Night
- Deborah Warner – Medea
- 2004: Jack O'Brien – Henry IV, Parts 1 and 2
- Doug Hughes – Frozen
- Moises Kaufman – I Am My Own Wife
- David Leveaux – Jumpers
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- 2005: Doug Hughes – Doubt: A Parable
- John Crowley – The Pillowman
- Scott Ellis – Twelve Angry Men
- Joe Mantello – Glengarry Glen Ross
- 2006: Nicholas Hytner – The History Boys
- Wilson Milam – The Lieutenant of Inishmore
- Bartlett Sher – Awake and Sing!
- Daniel J. Sullivan – Rabbit Hole
- 2007: Jack O'Brien – The Coast of Utopia
- Michael Grandage – Frost/Nixon
- David Grindley – Journey's End
- Melly Still – Coram Boy
- 2008: Anna D. Shapiro – August: Osage County
- Maria Aitken – The 39 Steps
- Conor McPherson – The Seafarer
- Matthew Warchus – Boeing Boeing
- 2009: Matthew Warchus – God of Carnage
- Phyllida Lloyd – Mary Stuart
- Bartlett Sher – Joe Turner's Come and Gone
- Matthew Warchus – The Norman Conquests
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