| 5th San Diego Film Critics Society Awards (2000) |
| Best Film: |
| Almost Famous |
| Best Director: |
| Cameron Crowe - Almost Famous |
| Best Actor: |
| Russell Crowe - Gladiator |
| Best Actress (tie): |
| Laura Linney - You Can Count on Me | |
| Julia Roberts - Erin Brockovich |
| Best Supporting Actor: |
| Benicio del Toro - Traffic |
| Best Supporting Actress: |
| Frances McDormand - Almost Famous |
| Best Screenplay - Adapted: |
| Chocolat - Robert Nelson Jacobs |
| Best Screenplay - Original: |
| Almost Famous - Cameron Crowe |
| Best Cinematography: |
| Gladiator - John Mathieson |
| Best Foreign Language Film: |
| The Colour of Paradise (Rang-e khoda) • Iran |
| Body of Work Award: |
| Joaquin Phoenix - Gladiator, Quills and The Yards |