Milan 1999 ATP
Final
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Richard Krajicek | m. | Greg Rusedski | 7-6(6) 6-7(5) 7-5 |
Semifinal
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Richard Krajicek | m. | Thomas Johansson | 6-2 6-4 |
| Greg Rusedski | m. | Hicham Arazi | 6-2 6-3 |
Perempat final
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Thomas Johansson | m. | Yevgeny Kafelnikov | 6-2 7-6(5) |
| Richard Krajicek | m. | Karol Kucera | 6-1 6-3 |
| Greg Rusedski | m. | Thomas Enqvist | 7-5 4-6 6-3 |
| Hicham Arazi | m. | Dominik Hrbaty | 6-4 6-2 |
Babak 16 besar
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Yevgeny Kafelnikov | m. | Byron Black | 6-3 6-2 |
| Thomas Johansson | m. | Davide Sanguinetti | 6-0 6-7(3) 6-2 |
| Richard Krajicek | m. | Nicolas Kiefer | 6-3 6-4 |
| Karol Kucera | m. | Guillaume Raoux | 6-2 6-0 |
| Thomas Enqvist | m. | David Prinosil | 6-4 7-5 |
| Greg Rusedski | m. | Petr Korda | 6-3 7-6(4) |
| Hicham Arazi | m. | Goran Ivanisevic | 3-6 6-3 6-4 |
| Dominik Hrbaty | m. | Jan Kroslak | 6-2 6-3 |
Babak 32 besar
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Yevgeny Kafelnikov | m. | Magnus Gustafsson | 6-2 3-6 6-3 |
| Byron Black | m. | Karim Alami | 6-1 1-6 7-6(4) |
| Davide Sanguinetti | m. | Jan Michael Gambill | 6-4 6-4 |
| Thomas Johansson | m. | Petr Luxa | 6-2 6-4 |
| Richard Krajicek | m. | Jeff Tarango | 6-4 6-2 |
| Nicolas Kiefer | m. | Cedric Pioline | 5-7 6-2 7-5 |
| Guillaume Raoux | m. | Daniel Vacek | 6-4 6-3 |
| Karol Kucera | m. | Rainer Schuettler | 7-6(2) 6-0 |
| Thomas Enqvist | m. | Marc Rosset | 6-1 6-3 |
| David Prinosil | m. | Andrei Pavel | 7-6(5) 6-3 |
| Petr Korda | m. | Wayne Ferreira | 6-3 6-4 |
| Greg Rusedski | m. | Gianluca Pozzi | 6-2 6-1 |
| Goran Ivanisevic | m. | Jan Siemerink | 6-3 0-6 7-6(1) |
| Hicham Arazi | m. | Bohdan Ulihrach | 7-5 6-4 |
| Dominik Hrbaty | m. | Stefano Pescosolido | 6-3 6-7(3) 6-2 |
| Jan Kroslak | m. | Tim Henman | 2-6 7-6(8) 6-4 |
Data: Jeff Sackmann / Tennis Abstract — CC BY-NC-SA 4.0