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