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