San Jose 1999 ATP
Final
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Mark Philippoussis | m. | Cecil Mamiit | 6-3 6-2 |
Semifinal
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Mark Philippoussis | m. | Pete Sampras | W/O |
| Cecil Mamiit | m. | Michael Chang | 3-6 6-3 6-4 |
Perempat final
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Pete Sampras | m. | Bernd Karbacher | 7-5 6-3 |
| Mark Philippoussis | m. | Justin Gimelstob | 6-2 3-6 7-6(0) |
| Michael Chang | m. | Christian Ruud | 6-1 7-5 |
| Cecil Mamiit | m. | Mark Woodforde | 7-6(5) 4-6 6-3 |
Babak 16 besar
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Pete Sampras | m. | Martin Rodriguez | 7-5 6-3 |
| Bernd Karbacher | m. | Sebastien Lareau | 6-3 6-7(5) 6-3 |
| Mark Philippoussis | m. | John Van Lottum | 6-2 6-1 |
| Justin Gimelstob | m. | Chris Woodruff | 6-4 7-6(3) |
| Christian Ruud | m. | Paul Goldstein | 6-1 7-6(4) |
| Michael Chang | m. | Franco Squillari | 6-4 7-6(5) |
| Mark Woodforde | m. | Ramon Delgado | 6-2 6-3 |
| Cecil Mamiit | m. | Andre Agassi | 0-6 6-6 DEF |
Babak 32 besar
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Pete Sampras | m. | Galo Blanco | 6-4 6-4 |
| Martin Rodriguez | m. | Alejandro Hernandez | 6-4 6-7(2) 6-3 |
| Bernd Karbacher | m. | Stefan Koubek | 6-3 6-2 |
| Sebastien Lareau | m. | Mariano Zabaleta | 6-2 6-1 |
| Mark Philippoussis | m. | Sargis Sargsian | 6-7(2) 7-5 6-3 |
| John Van Lottum | m. | Jim Courier | 6-4 7-6(4) |
| Chris Woodruff | m. | Ronald Agenor | 2-6 6-2 6-3 |
| Justin Gimelstob | m. | Jan Michael Gambill | 6-3 7-6(6) |
| Christian Ruud | m. | Mariano Puerta | 6-2 4-6 6-3 |
| Paul Goldstein | m. | Carlos Costa | 4-6 6-4 6-4 |
| Franco Squillari | m. | Albert Portas | 6-1 3-6 6-2 |
| Michael Chang | m. | Fernando Meligeni | 6-3 6-2 |
| Ramon Delgado | m. | Brett Steven | 5-7 6-4 7-5 |
| Mark Woodforde | m. | Steve Campbell | 6-3 3-6 7-5 |
| Cecil Mamiit | m. | Kenneth Carlsen | 2-6 6-3 7-5 |
| Andre Agassi | m. | Todd Woodbridge | 6-2 6-1 |