1999 Sybase Open – Singles
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Andre Agassi was the defending champion, but was defaulted in his second round match against Cecil Mamiit for swearing at a line judge.
Mark Philippoussis won the title, defeating Mamiit 6–3, 6–2 in the final.
Seeds
- United States Pete Sampras (semifinals, withdrew because of an ankle injury)
- United States Andre Agassi (second round, defaulted)
- Australia Mark Philippoussis (champion)
- United States Michael Chang (semifinals)
- Argentina Mariano Puerta (first round)
- United States Jan-Michael Gambill (first round)
- Argentina Mariano Zabaleta (first round)
- Paraguay Ramón Delgado (second round)
Draw
Key
- Q = Qualifier
- WC = Wild card
- LL = Lucky loser
- Alt = Alternate
- ITF = ITF entry
- PR = Protected ranking
- SR = Special ranking
- SE = Special exempt
- JE = Junior exempt
- JR = Junior Accelerator Programme entrant
- CO = College Accelerator Programme entrant
- NG = Next Gen Accelerator Program entrant
- w/o = Walkover
- r = Retired
- d = Defaulted
Finals
| Semifinals | Final | ||||||||||||
| 1 | United States Pete Sampras | ||||||||||||
| 3 | Australia Mark Philippoussis | w/o | |||||||||||
| 3 | Australia Mark Philippoussis | 6 | 6 | ||||||||||
| Q | United States Cecil Mamiit | 3 | 2 | ||||||||||
| 4 | United States Michael Chang | 6 | 3 | 4 | |||||||||
| Q | United States Cecil Mamiit | 3 | 6 | 6 |
Top half
| First round | Second round | Quarterfinals | Semifinals | ||||||||||||||||||||||||
| 1 | United States P Sampras | 6 | 6 | ||||||||||||||||||||||||
| Spain G Blanco | 4 | 4 | 1 | United States P Sampras | 7 | 6 | |||||||||||||||||||||
| Argentina M Rodríguez | 6 | 62 | 6 | Argentina M Rodríguez | 5 | 3 | |||||||||||||||||||||
| Q | Mexico A Hernández | 4 | 77 | 3 | 1 | United States P Sampras | 7 | 6 | |||||||||||||||||||
| Q | Germany B Karbacher | 6 | 6 | Q | Germany B Karbacher | 5 | 3 | ||||||||||||||||||||
| Austria S Koubek | 3 | 2 | Q | Germany B Karbacher | 6 | 65 | 6 | ||||||||||||||||||||
| Canada S Lareau | 6 | 6 | Canada S Lareau | 3 | 77 | 3 | |||||||||||||||||||||
| 7 | Argentina M Zabeleta | 2 | 1 | 1 | United States P Sampras | ||||||||||||||||||||||
| 3 | Australia M Philippoussis | 62 | 7 | 6 | 3 | Australia M Philippoussis | w/o | ||||||||||||||||||||
| Armenia S Sargsian | 77 | 5 | 3 | 3 | Australia M Philippoussis | 6 | 6 | ||||||||||||||||||||
| United States J Courier | 4 | 64 | Netherlands J van Lottum | 2 | 1 | ||||||||||||||||||||||
| Netherlands J van Lottum | 6 | 77 | 3 | Australia M Philippoussis | 6 | 3 | 77 | ||||||||||||||||||||
| Q | Haiti R Agénor | 6 | 2 | 3 | WC | United States J Gimelstob | 2 | 6 | 60 | ||||||||||||||||||
| WC | United States C Woodruff | 2 | 6 | 6 | WC | United States C Woodruff | 4 | 63 | |||||||||||||||||||
| WC | United States J Gimelstob | 6 | 78 | WC | United States J Gimelstob | 6 | 77 | ||||||||||||||||||||
| 6 | United States J-M Gambill | 3 | 66 |
Bottom half
| First round | Second round | Quarterfinals | Semifinals | ||||||||||||||||||||||||
| 5 | Argentina M Puerta | 2 | 6 | 3 | |||||||||||||||||||||||
| Norway C Ruud | 6 | 4 | 6 | Norway C Ruud | 6 | 77 | |||||||||||||||||||||
| Spain C Costa | 6 | 4 | 4 | WC | United States P Goldstein | 1 | 64 | ||||||||||||||||||||
| WC | United States P Goldstein | 4 | 6 | 6 | Norway C Ruud | 1 | 5 | ||||||||||||||||||||
| Argentina F Squillari | 6 | 3 | 6 | 4 | United States M Chang | 6 | 7 | ||||||||||||||||||||
| Spain A Portas | 1 | 6 | 2 | Argentina F Squillari | 4 | 65 | |||||||||||||||||||||
| Brazil F Meligeni | 3 | 2 | 4 | United States M Chang | 6 | 77 | |||||||||||||||||||||
| 4 | United States M Chang | 6 | 6 | 4 | United States M Chang | 6 | 3 | 4 | |||||||||||||||||||
| 8 | Paraguay R Delgado | 5 | 6 | 7 | Q | United States C Mamiit | 3 | 6 | 6 | ||||||||||||||||||
| New Zealand B Steven | 7 | 4 | 5 | 8 | Paraguay R Delgado | 2 | 3 | ||||||||||||||||||||
| United States S Campbell | 3 | 6 | 5 | Australia M Woodforde | 6 | 6 | |||||||||||||||||||||
| Australia M Woodforde | 6 | 3 | 7 | Australia M Woodforde | 65 | 6 | 3 | ||||||||||||||||||||
| Q | United States C Mamiit | 2 | 6 | 7 | Q | United States C Mamiit | 77 | 4 | 6 | ||||||||||||||||||
| Denmark K Carlsen | 6 | 3 | 5 | Q | United States C Mamiit | 0 | 6 | ||||||||||||||||||||
| Australia T Woodbridge | 2 | 1 | 2 | United States A Agassi | 6 | 6d | |||||||||||||||||||||
| 2 | United States A Agassi | 6 | 6 |