Cincinnati Masters 1999 ATP
Final
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Pete Sampras | m. | Patrick Rafter | 7-6(7) 6-3 |
Semifinal
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Pete Sampras | m. | Andre Agassi | 7-6(7) 6-4 |
| Patrick Rafter | m. | Yevgeny Kafelnikov | 6-4 6-2 |
Perempat final
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Pete Sampras | m. | Richard Krajicek | 6-4 6-2 |
| Andre Agassi | m. | Gustavo Kuerten | 6-2 7-6(10) |
| Yevgeny Kafelnikov | m. | Tim Henman | 7-5 7-5 |
| Patrick Rafter | m. | Michael Chang | 6-2 6-1 |
Babak 16 besar
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Pete Sampras | m. | Rainer Schuettler | 7-5 7-6(2) |
| Richard Krajicek | m. | Justin Gimelstob | 6-4 6-2 |
| Andre Agassi | m. | Jiri Novak | 7-6(3) 7-6(5) |
| Gustavo Kuerten | m. | Tommy Haas | 7-5 7-5 |
| Tim Henman | m. | Nicolas Kiefer | 6-4 6-1 |
| Yevgeny Kafelnikov | m. | Chris Woodruff | 6-4 6-4 |
| Michael Chang | m. | Cedric Pioline | 6-1 6-4 |
| Patrick Rafter | m. | Nicolas Lapentti | 6-2 6-3 |
Babak 32 besar
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Pete Sampras | m. | Jan Siemerink | 7-6(9) 6-4 |
| Rainer Schuettler | m. | Magnus Larsson | 7-5 7-6(5) |
| Justin Gimelstob | m. | Todd Martin | 6-4 6-4 |
| Richard Krajicek | m. | Ivan Ljubicic | 6-1 6-3 |
| Andre Agassi | m. | Arnaud Di Pasquale | 6-4 6-1 |
| Jiri Novak | m. | Albert Costa | 7-6(3) 7-6(6) |
| Tommy Haas | m. | Fabrice Santoro | 6-0 6-7(1) 6-3 |
| Gustavo Kuerten | m. | Alberto Martin | 6-2 6-3 |
| Tim Henman | m. | John Van Lottum | 6-2 6-1 |
| Nicolas Kiefer | m. | Paul Goldstein | 2-6 6-4 7-6(10) |
| Chris Woodruff | m. | Thomas Enqvist | 6-1 7-5 |
| Yevgeny Kafelnikov | m. | Jonas Bjorkman | 6-1 6-4 |
| Michael Chang | m. | Alex Corretja | 6-3 6-7(5) 6-2 |
| Cedric Pioline | m. | Jim Courier | 6-7(5) 7-6(4) 2-0 RET |
| Nicolas Lapentti | m. | Jan Michael Gambill | 6-0 7-6(3) |
| Patrick Rafter | m. | Daniel Vacek | 7-6(3) 6-3 |