* 2000: Dinner with Friends – Donald Margulies
o King Hedley II – August Wilson
o In the Blood – Suzan-Lori Parks
* 2001: Proof – David Auburn
o The Play About the Baby – Edward Albee
o The Waverly Gallery – Kenneth Lonergan
* 2002: Topdog/Underdog – Suzan-Lori Parks
o The Glory of Living – Rebecca Gilman
o Yellowman – Dael Orlandersmith
* 2003: Anna in the Tropics – Nilo Cruz
o Take Me Out – Richard Greenberg
o The Goat, or Who Is Sylvia? – Edward Albee
* 2004: I Am My Own Wife – Doug Wright
o Man from Nebraska – Tracy Letts
o Omnium Gatherum – Theresa Rebeck and Alexandra Gersten-Vassilaros
* 2005 Doubt: A Parable – John Patrick Shanley
o The Clean House – Sarah Ruhl
o Thom Pain (Based on Nothing) – Will Eno
* 2006: no award
o Miss Witherspoon – Christopher Durang
o The Intelligent Design of Jenny Chow – Rolin Jones
o Red Light Winter – Adam Rapp
* 2007: Rabbit Hole – David Lindsay-Abaire
o Bulrusher – Eisa Davis
o Orpheus X – Rinde Eckert
o Elliot, a Soldier's Fugue – Quiara Alegría Hudes
* 2008 August: Osage County – Tracy Letts
o Yellow Face – David Henry Hwang
o Dying City – Christopher Shinn