Friday, September 3, 1999
| Men's -- Second Round |
| Match |
Result |
| Gustavo Kuerten (5) def. Paul Haarhuis |
6-3, 7-6 (7-4), 3-6, 6-2 |
| Todd Martin (7) def. Richey Reneberg |
6-4, 6-3, 3-6, 6-1 |
| Greg Rusedski (9) def. David Prinosil |
6-4, 6-3, 6-1 |
| Tommy Haas (14) def. Mariano Puerta |
6-3, 6-2, 2-6, 6-7 (3-7), 6-1 |
| Fredrik Jonsson def. Nicolas Lapentti (16) |
6-4, 5-7, 6-4, 7-5 |
| Fabrice Santoro def. Jan-Michael Gambill |
6-4, 6-2, 3-6, 6-7 (7-9), 4-4, retired |
| Goran Ivanisevic def. Cristiano Caratti |
6-1, 4-6, 6-2, 2-6, 6-4 |
| Magnus Norman def. Gianluca Pozzi |
6-4, 6-3, 6-4 |
| Slava Dosedel def. Fernando Meligeni |
7-5, 6-1, 6-3 |
| Magnus Larsson def. Younes El Aynaoui |
6-3, 6-4, 3-6, 6-3 |
| Cedric Pioline def. Lars Burgsmuller |
7-6 (7-5), 1-6, 6-3, 3-6, 6-2 |
| Jiri Novak def. Marat Safin |
6-2, 5-7, 6-4, 3-6, 6-2 |
| Peter Wessels def. Mark Woodforde |
3-6, 7-5, 7-6 (10-8), 7-6 (7-4) |
| Chris Woodruff def. Christian Ruud |
6-2, 6-3, 6-3 |
| Hicham Arazi def. Fernando Vicente |
3-6, 6-3, 6-3, 7-6 (7-4) |
| Richard Fromberg def. Markus Hipfl |
5-7, 6-3, 6-4, 6-4 |
| Women's -- Third Round |
| Match |
Result |
| Martina Hingis (1) def. Sandra Kloesel |
6-3, 6-1 |
| Anke Huber def. Jana Novotna (8) |
6-3, 6-2 |
| Arantxa Sanchez-Vicario (10) def. Patty Schnyder |
6-2, 6-2 |
| Barbara Schett (12) def. Virginia Ruano Pascual |
6-1, 6-0 |
| Mary Joe Fernandez def. Dominique Van Roost (13) |
7-5, 6-0 |
| Amelie Mauresmo (15) def. Tara Snyder |
6-4, 6-3 |
| Elena Likhovtseva def. Irina Spirlea |
6-1, 6-3 |
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