- 2000: Michael Blakemore – Kiss Me, Kate
- Gabriel Barre – The Wild Party
- Susan Stroman – Contact and The Music Man
- 2001: Susan Stroman – The Producers
- Christopher Ashley – The Rocky Horror Show
- Wilfredo Medina – The Bubbly Black Girl Sheds Her Chameleon Skin
- Jack O'Brien – The Full Monty
- John Rando – Urinetown
- Scott Schwartz – Bat Boy: The Musical
- 2002: Michael Mayer – Thoroughly Modern Millie
- Nicholas Hytner – Sweet Smell of Success
- James Lapine – Into the Woods
- Trevor Nunn – Oklahoma!
- Scott Schwartz – Tick, Tick... Boom!
- George C. Wolfe – Elaine Stritch: At Liberty
- 2003: Jack O'Brien – Hairspray
- James Lapine – Amour
- David Leveaux – Nine
- Baz Luhrmann – La bohème
- Joe Mantello – A Man of No Importance
- Twyla Tharp – Movin' Out
- 2004: Joe Mantello – Wicked
- Jeff Calhoun – Big River
- Pamela Hunt – The Musical of Musicals: The Musical
- Joe Mantello – Assassins
- Kathleen Marshall – Wonderful Town
- George C. Wolfe – Caroline, or Change
- 2005: James Lapine – The 25th Annual Putnam County Spelling Bee
- Matthew Bourne – Play Without Words
- Jack Cummings III – The Audience
- Mark Dornford-May – The Mysteries
- Mike Nichols – Spamalot
- Bartlett Sher – The Light in the Piazza
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- 2006: John Doyle – Sweeney Todd: The Demon Barber of Fleet Street
- Michael Greif – Grey Gardens
- Daniel Finzi Pasca – Rain
- Des McAnuff – Jersey Boys
- Casey Nicholaw – The Drowsy Chaperone
- Kathleen Marshall – The Pajama Game
- 2007: Michael Mayer – Spring Awakening
- John Doyle – Company
- Thomas Kail – In the Heights
- Jerry Mitchell – Legally Blonde
- Harold Prince – LoveMusik
- Alex Timbers – Gutenberg! The Musical!
- 2008: Bartlett Sher – South Pacific
- Christopher Ashley – Xanadu
- Sam Buntrock – Sunday in the Park with George
- David Cromer – Adding Machine
- John Doyle – A Catered Affair
- Bob McGrath – The Slug Bearers of Kayrol Island
- 2009: Stephen Daldry – Billy Elliot the Musical
- Walter Bobbie – Irving Berlin's White Christmas
- Joe Mantello – 9 to 5
- Jason Moore – Shrek the Musical
- Diane Paulus – Hair
- Stuart Ross – Enter Laughing the Musical
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