Las Vegas 1999 ATP
Final
| Winner | Loser | Score | |
|---|---|---|---|
| Jan Michael Gambill | d. | Lleyton Hewitt | 7-6(2) 4-6 6-4 |
Semifinals
| Winner | Loser | Score | |
|---|---|---|---|
| Jan Michael Gambill | d. | Andre Agassi | 5-4 RET |
| Lleyton Hewitt | d. | Mark Woodforde | 6-2 6-2 |
Quarterfinals
| Winner | Loser | Score | |
|---|---|---|---|
| Jan Michael Gambill | d. | Justin Gimelstob | 4-6 6-4 6-1 |
| Andre Agassi | d. | Cedric Pioline | 6-4 6-1 |
| Mark Woodforde | d. | Goran Ivanisevic | 7-6(6) 4-6 6-1 |
| Lleyton Hewitt | d. | Jerome Golmard | 6-1 3-0 RET |
Round of 16
| Winner | Loser | Score | |
|---|---|---|---|
| Jan Michael Gambill | d. | Pete Sampras | 4-6 6-3 6-4 |
| Justin Gimelstob | d. | Fernando Vicente | 7-6(5) 6-2 |
| Andre Agassi | d. | Mariano Zabaleta | 6-2 6-0 |
| Cedric Pioline | d. | Andrew Ilie | 6-1 6-2 |
| Mark Woodforde | d. | Francisco Clavet | 6-3 3-6 6-1 |
| Goran Ivanisevic | d. | Hernan Gumy | 6-4 6-4 |
| Jerome Golmard | d. | Nicolas Lapentti | 3-5 RET |
| Lleyton Hewitt | d. | Patrick Rafter | 7-6(5) 6-1 |
Round of 32
| Winner | Loser | Score | |
|---|---|---|---|
| Pete Sampras | d. | Ramon Delgado | 7-6(2) 6-2 |
| Jan Michael Gambill | d. | Franco Squillari | 3-6 6-3 6-4 |
| Fernando Vicente | d. | Jason Stoltenberg | 7-6(3) 7-5 |
| Justin Gimelstob | d. | Thomas Muster | 6-4 7-5 |
| Andre Agassi | d. | Fernando Meligeni | 3-6 7-5 6-3 |
| Mariano Zabaleta | d. | Slava Dosedel | 5-7 6-2 6-2 |
| Andrew Ilie | d. | Chris Woodruff | 6-3 2-6 7-6(7) |
| Cedric Pioline | d. | Mariano Puerta | 7-6(6) 6-2 |
| Mark Woodforde | d. | Tommy Haas | 6-3 5-7 6-2 |
| Francisco Clavet | d. | Nicolas Escude | 6-7(5) 6-1 6-2 |
| Hernan Gumy | d. | Sjeng Schalken | 3-6 7-5 6-1 |
| Goran Ivanisevic | d. | Scott Draper | 6-3 3-6 6-3 |
| Jerome Golmard | d. | Gustavo Kuerten | 6-3 3-6 6-3 |
| Nicolas Lapentti | d. | Andrei Pavel | 6-3 4-6 6-1 |
| Lleyton Hewitt | d. | Magnus Norman | 6-3 7-5 |
| Patrick Rafter | d. | Alex Obrien | 6-3 6-4 |