| 20th Boston Society of Film Critics Awards (1999) |
| Best Film: |
| Three Kings |
| Best Director: |
| David O. Russell - Three Kings |
| Best Actor: |
| Jim Carrey - Man on the Moon |
| Best Actress: |
| Hilary Swank - Boys Don't Cry |
| Best Supporting Actor: |
| Christopher Plummer - The Insider |
| Best Supporting Actress: |
| Chloë Sevigny - Boys Don't Cry |
| Best Screenplay: |
| Charlie Kaufman - Being John Malkovich |
| Best Cinematography: |
| Emmanuel Lubezki - Sleepy Hollow |
| Best Foreign-Language Film: |
| All About My Mother (Todo sobre mi madre) • Spain/France |
| Best Documentary: |
| Hands on a Hard Body: The Documentary |
| Best New Filmmaker: |
| Kimberly Peirce - Boys Don't Cry |