| 4th Florida Film Critics Circle Awards (1999) |
| Best Film: |
| Magnolia |
| Best Director: |
| Sam Mendes - American Beauty |
| Best Cast: |
| Magnolia |
| Best Actor: |
| Kevin Spacey - American Beauty |
| Best Actress: |
| Hilary Swank - Boys Don't Cry |
| Best Supporting Actor: |
| Haley Joel Osment - The Sixth Sense |
| Best Supporting Actress: |
| Catherine Keener - Being John Malkovich |
| Best Screenplay: |
| Election - Alexander Payne and Jim Taylor |
| Best Cinematography: |
| Snow Falling on Cedars and Bringing Out the Dead - Robert Richardson |
| Best Foreign Language Film: |
| Run Lola Run (Lola rennt) • Germany |
| Best Documentary: |
| Buena Vista Social Club |
| Best Animated Film: |
| The Iron Giant |
| Best Newcomer: |
| Spike Jonze - Being John Malkovich and Three Kings |
| Pauline Kael Breakout Award: |
| Spike Jonze - Being John Malkovich and Three Kings |
| Golden Orange for Outstanding Contribution to Film: |
| Dan Myrick, Eduardo Sanchez, Gregg Hale, Robin Cowie, and Michael Monello |