Winnetka CH 1999 ATP
Final
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Alex Obrien | m. | Max Mirnyi | 6-2 6-2 |
Semifinal
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Alex Obrien | m. | Michael Tebbutt | 7-6(5) 6-3 |
| Max Mirnyi | m. | Paul Goldstein | 6-4 6-2 |
Perempat final
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Michael Tebbutt | m. | Gabriel Trifu | W/O |
| Alex Obrien | m. | Mashiska Washington | 6-4 6-4 |
| Max Mirnyi | m. | Mark Nielsen | 6-4 7-5 |
| Paul Goldstein | m. | Michel Kratochvil | 7-6(3) 4-6 6-4 |
Babak 16 besar
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Gabriel Trifu | m. | Cecil Mamiit | 6-0 7-5 |
| Michael Tebbutt | m. | Hideki Kaneko | 6-1 6-3 |
| Alex Obrien | m. | Michael Russell | 6-1 6-2 |
| Mashiska Washington | m. | Taylor Dent | 7-6(6) 6-2 |
| Mark Nielsen | m. | James Blake | 7-6(3) 6-4 |
| Max Mirnyi | m. | Oren Motevassel | 6-3 4-6 6-3 |
| Michel Kratochvil | m. | Harel Levy | 7-5 6-2 |
| Paul Goldstein | m. | Kevin Kim | 6-3 6-2 |
Babak 32 besar
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Cecil Mamiit | m. | Thomas Blake | 6-3 6-1 |
| Gabriel Trifu | m. | Jim Thomas | 6-4 6-1 |
| Michael Tebbutt | m. | James Sekulov | 6-3 7-6(1) |
| Hideki Kaneko | m. | Lior Mor | 7-5 7-5 |
| Alex Obrien | m. | David Caldwell | 6-7(4) 6-4 7-5 |
| Michael Russell | m. | David Dilucia | 6-3 7-5 |
| Mashiska Washington | m. | Alexander Reichel | 7-5 6-4 |
| Taylor Dent | m. | Andre Sa | 7-5 6-1 |
| James Blake | m. | Maurice Ruah | 7-5 6-4 |
| Mark Nielsen | m. | Michael Sell | 4-6 6-4 6-3 |
| Oren Motevassel | m. | Michael Hill | 4-6 6-0 6-3 |
| Max Mirnyi | m. | Mark Draper | 7-6(4) 6-4 |
| Harel Levy | m. | Alexander Popp | 3-6 6-4 6-4 |
| Michel Kratochvil | m. | Paradorn Srichaphan | 6-4 6-2 |
| Kevin Kim | m. | Steve Campbell | 3-6 6-2 6-1 |
| Paul Goldstein | m. | Mark Knowles | 6-2 2-6 6-2 |