Winnetka CH 1990 ATP
Final
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Cristiano Caratti | m. | Chris Garner | 7-6 6-1 |
Semifinal
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Chris Garner | m. | Chris Pridham | 3-6 6-4 6-1 |
| Cristiano Caratti | m. | Grant Stafford | 6-3 6-3 |
Perempat final
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Chris Garner | m. | Todd Martin | 2-6 6-2 6-4 |
| Chris Pridham | m. | Nuno Marques | 6-3 6-4 |
| Grant Stafford | m. | Tommy Ho | 6-4 6-2 |
| Cristiano Caratti | m. | Mark Petchey | 3-6 7-6 6-1 |
Babak 16 besar
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Todd Martin | m. | Bryan Shelton | 7-5 6-4 |
| Chris Garner | m. | Buff Farrow | 6-1 6-1 |
| Nuno Marques | m. | Johan Carlsson | 6-2 6-3 |
| Chris Pridham | m. | Scott Patridge | 3-6 6-3 7-6 |
| Grant Stafford | m. | Royce Deppe | 7-5 6-1 |
| Tommy Ho | m. | Wayne Ferreira | 6-2 6-4 |
| Cristiano Caratti | m. | Ugo Colombini | 7-5 6-4 |
| Mark Petchey | m. | Miguel Nido | 6-3 6-2 |
Babak 32 besar
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Bryan Shelton | m. | Ville Jansson | 6-3 2-6 6-4 |
| Todd Martin | m. | Menno Oosting | 6-2 6-4 |
| Buff Farrow | m. | Jett Jones | 6-0 6-0 |
| Chris Garner | m. | Diego Nargiso | 6-4 1-0 DEF |
| Nuno Marques | m. | Peter Nyborg | 6-4 6-2 |
| Johan Carlsson | m. | David Lewis | 4-6 6-2 6-4 |
| Scott Patridge | m. | Philip Johnson | 6-3 6-0 |
| Chris Pridham | m. | Luis Herrera | 7-6 6-7 6-4 |
| Grant Stafford | m. | Gianluca Pozzi | 6-4 6-2 |
| Royce Deppe | m. | Henrik Holm | 3-6 6-4 6-4 |
| Tommy Ho | m. | Mike Holten | 6-2 0-6 6-4 |
| Wayne Ferreira | m. | Martin Laurendeau | 6-4 6-4 |
| Ugo Colombini | m. | Bong Soo Kim | 6-4 7-6 |
| Cristiano Caratti | m. | Steve Bryan | 2-6 6-3 6-0 |
| Mark Petchey | m. | Michael Robertson | 6-4 6-3 |
| Miguel Nido | m. | Danny Sapsford | 6-2 7-6 |