The Drama Desk, a group of 150 theater critics and reporters, announced the awards on May 14, 2000.
| Outstanding Play | Copenhagen |
| Outstanding Musical | Contact |
| Outstanding Musical Revival | Kiss Me, Kate |
| Outstanding Play Revival | The Real Thing |
| Outstanding One-Person Show | Barry Humphries, Dame Edna: The Royal Tour |
| Unique Theatrical Experience | Charlie Victor Romeo |
| Best Actor in a Play | Stephen Dillane, The Real Thing |
| Best Actress in a Play | Eileen Heckart, The Waverly Gallery |
| Best Featured Actor in a Play | Roy Dotrice, A Moon for the Misbegotten |
| Best Featured Actress in a Play | Marylouise Burke, Fuddy Meers |
| Best Actor in a Musical | Brian Stokes Mitchell, Kiss Me, Kate |
| Best Actress in a Musical | Heather Headley, Aida |
| Best Featured Actor in a Musical | Stephen Spinella, The Dead |
| Best Featured Actress in a Musical | Karen Ziemba, Contact |
| Best Director of a Play | Michael Blakemore, Copenhagen |
| Best Director of a Musical | Michael Blakemore, Kiss Me, Kate |
| Best Choreography | Susan Stroman, Contact |
| Best Music | Andrew Lippa, The Wild Party—MTC |
| Best Lyrics | Stephen Sondheim, Saturday Night |
| Outstanding Orchestrations | Don Sebesky, Kiss Me, Kate |
| Outstanding Set Design of a Play | David Gallo, Jitney |
| Outstanding Set Design of a Musical | Robin Wagner, Kiss Me, Kate |
| Special Awards | Alexander H. Cohen (posthumous)—Lifelong commitment to excellence in theatre |
| Barnard Hughes and Helen Stenborg—Shared Lifetime Achievement |
| Cast of Jitney—Outstanding Ensemble Performance |
Information Please® Database, © 2007 Pearson Education, Inc. All rights reserved.