The Drama Desk, a group of 150 theater critics and reporters, announced the awards on May 9, 1999.
| Outstanding Play | Wit |
| Outstanding Musical | Parade |
| Outstanding Musical Revival | Your a Good Man, Charlie Brown |
| Outstanding Play Revival | Death of a Salesman |
| The Iceman Cometh |
| Outstanding One-Person Show | David Hare, Via Dolorosa |
| Unique Theatrical Experience | |
| Best Actor in a Play | Brian Dennehy, Death of a Salesman |
| Best Actress in a Play | Kathleen Chalfant, Wit |
| Best Featured Actor in a Play | Kevin Anderson, Death of a Salesman |
| Best Featured Actress in a Play | Anna Friel, Closer |
| Best Actor in a Musical | Brent Carver, Parade |
| Best Actress in a Musical (tie) | Carolee Carmello, Parade |
| Bernadette Peters, Annie Get Your Gun |
| Best Featured Actor in a Musical | Roger Bart, You're a Good Man, Charlie Brown |
| Best Featured Actress in a Musical | Kristen Chenoweth, You're a Good Man, Charlie Brown |
| Best Director of a Play | Trevor Nunn, Not about Nightingales |
| Best Director of a Musical | Matthew Bourne, Swan Lake |
| Best Choreography | Matthew Bourne, Swan Lake |
| Best Music | Jason Robert Brown, Parade |
| Best Lyrics | Gerard Alessandrini, Forbidden Broadway Cleans Up Its |
| Outstanding Book of a Musica | Alfred Uhry, Parade |
| Outstanding Orchestrations | Don Sebesky, Parade |
| Outstanding Set Design of a Play | Richard Hoover, Not about Nightingales |
| Outstanding Set Design of a Musical | Lez Brotherson, Swan Lake |
| Special Awards | Al Hirschfeld (lifetime achievement) |
| Sony Classical (for its Columbia Broadway Masterworks Series) |
| The Actor's Fund |
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