- 2000: Michael Blakemore – Copenhagen
- Thomas Hulce and Jane Jones – The Cider House Rules
- Marion McClinton – Jitney
- Daniel J. Sullivan – Dinner with Friends
- James Lapine – Dirty Blonde
- Michael Mayer – Uncle Vanya
- 2001: Jack O'Brien – The Invention of Love
- Mark Brokaw – Lobby Hero
- Michael Greif – Dogeaters
- Philip Seymour Hoffman – Jesus Hopped the 'A' Train
- Jonathan Kent – Richard II
- Matthew Warchus – The Unexpected Man
- 2002: Mary Zimmerman – Metamorphoses
- Carl Forsman – The Voice of the Turtle
- Neil LaBute – The Shape of Things
- Bartlett Sher – Cymbeline
- Howard Davies – Private Lives
- Richard Eyre – The Crucible
- 2003: Robert Falls – Long Day's Journey into Night
- Philip Seymour Hoffman – Our Lady of 121st Street
- Sam Mendes – Twelfth Night and Uncle Vanya
- Deborah Warner – Medea
- Joe Mantello – Take Me Out
- 2004: Jack O'Brien – Henry IV
- Hilary Adams – Moby Dick
- Dexter Bullard – Bug
- Edward Hall – A Midsummer Night's Dream
- Kenny Leon – A Raisin in the Sun
- Moisés Kaufman – I Am My Own Wife
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- 2005: Doug Hughes – Doubt
- Josh Carlebach – Frankenstein
- Scott Elliott – Hurlyburly
- Edward Hall – Rose Rage
- Joe Mantello – Glengarry Glen Ross
- Scott Ellis – Twelve Angry Men
- 2006: Nicholas Hytner – The History Boys
- Alan Ayckbourn – Private Fears in Public Places
- Gisela Cardenas – Agamemnon
- Daniel J. Sullivan – Stuff Happens
- Robert Wilson – Peer Gynt
- Jerry Zaks – The Caine Mutiny Court-Martial
- 2007: Jack O'Brien – The Coast of Utopia
- Declan Donnellan – Twelfth Night
- Ciaran O'Reilly – The Hairy Ape
- Tom Ridgely – Marco Millions (based on lies)
- Michael Grandage – Frost/Nixon
- Doug Hughes – Inherit the Wind
- 2008: Anna D. Shapiro – August: Osage County
- David Schweizer – Horizon
- Leigh Silverman – From Up Here
- Jonathan Silverstein – The Dining Room
- Matthew Warchus – Boeing-Boeing
- Deborah Warner – Happy Days
- 2009: Matthew Warchus – The Norman Conquests
- Sarah Benson – Blasted
- Michael Blakemore – Blithe Spirit
- Garry Hynes – The Cripple of Inishmaan
- Terry Kinney – reasons to be pretty
- Kate Whoriskey – Ruined
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