Winners of the 1999 Academy Awards
| Category | Winner | Distributor | Gross ($M) |
| Picture | American Beauty | DreamWorks | 116.7 |
| Director | Sam Mendes, American Beauty | DreamWorks | 116.7 |
| Actor | Kevin Spacey, American Beauty | DreamWorks | 116.7 |
| Actress | Hilary Swank, Boys Don't Cry | Fox Searchlight | 9.3 |
| Supporting Actor | Michael Caine, The Cider House Rules | Miramax | 53.0 |
| Supporting Actress | Angelina Jolie, Girl, Interrupted | Sony | 28.6 |
| Original Screenplay | American Beauty | DreamWorks | 116.7 |
| Adapted Screenplay | The Cider House Rules | Miramax | 53.0 |
| Art Direction | Sleepy Hollow | Paramount | 100.6 |
| Cinematography | American Beauty | DreamWorks | 116.7 |
| Costume Design | Topsy-Turvy | USA Films | 5.8 |
| Editing | The Matrix | Warner Bros. | 171.4 |
| Foreign Language Film | All About My Mother | Sony Classics | 7.2 |
| Makeup | Topsy-Turvy | USA Films | 5.8 |
| Original Score | The Red Violin | Lions Gate | 10.0 |
| Song | "You'll Be in My Heart", Tarzan | Buena Vista | 171.1 |
| Sound | The Matrix | Warner Bros. | 171.4 |
| Sound Effects Editing | The Matrix | Warner Bros. | 171.4 |
| Visual Effects | The Matrix | Warner Bros. | 171.4 |
| Documentary Feature | One Day in September | ||
| Documentary Short | King Gimp | ||
| Short - Animated | The Old Man and the Sea | ||
| Short - Live Action | My Mother Dreams … |
Last Updated : April 3, 2000
Written by Gitesh Pandya