The 1999–2000 Obie Awards, honoring distinguished achievement in Off-Broadway and Off-Off-Broadway productions, were presented on May 15, 2000, at New York's Webster Hall.
| Best Production: | Ben Katcho, Michael Gordon, David Lang, Julia Wolfe, Bob McGrath, The Carbon Copy Building |
| Playwriting: | Harley Granville Barker, Waste |
| Direction: | Marion McClinton, Jitney |
| Performance: | Colm Meaney, The Cider House Rules: Part One, Here in St. Cloud's; |
| Lynne Thigpen, Jar the Floor; |
| Elizabeth Marvel, A Streetcar Named Desire; |
| Christopher Evan Welch, A Streetcar Named Desire; |
| Charlayne Woodard, In the Blood; |
| Lola Pashalinski, Gertrude and Alice; |
| Dominique Dibbell, Jet Lag; |
| Cynthia Hopkins, Another Telepathic Thing; |
| Debra Monk, The Time of the Cuckoo; |
| Eddie Korbich, Taking a Chance on Love; |
| Byron Jennings, Waste; |
| Eileen Heckart, The Waverly Gallery; |
| The cast of Jitney, excellence of ensemble performance |
| Design: | Jan Hartley, for sustained excellence of projection design; |
| Mark Dendy, choreography forThe Wild Party; |
| Christopher Akerlind, for sustained excellence of lighting design; |
| David Gallo, for sustained excellence of set design; |
| Susan Hilferty , for sustained excellence of costume design; |
| Special Citations: | Jan Lauwers/Needcompany, Morning Song; |
| Sarah E. Johnson, Lava Love; |
| Joe Mantello and Marc Wolf, Another American: Asking and Telling; |
| The Builders Association and Diller + Scofidio, Jet Lag; |
| Jesusa Rodriguez and Liliana Felipe, Las Horas de Belen—A Book of Hours; |
| Bill Talen; The Reverend Billy; |
| Maria Irene Fornes; Letters From Cuba; |
| Deb Margolin, sustained excellence of performance |
| Sustained Achievement: | Ping Chong |
| Ross Wetzsteon Award: | The Foundry |
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