Winnetka CH 1989 ATP
Final
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Brian Garrow | m. | Todd Martin | 6-4 6-2 |
Semifinal
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Todd Martin | m. | Bryan Shelton | 6-4 6-4 |
| Brian Garrow | m. | Robbie Weiss | 6-3 6-4 |
Perempat final
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Todd Martin | m. | Steve Bryan | 6-3 6-4 |
| Brian Garrow | m. | Ville Jansson | 1-6 6-3 6-3 |
| Robbie Weiss | m. | Tom Mercer | 6-4 6-2 |
| Bryan Shelton | m. | Scott Warner | 6-1 6-2 |
Babak 16 besar
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Bryan Shelton | m. | Arkie Engle | 6-3 6-2 |
| Tom Mercer | m. | Buff Farrow | 3-6 6-4 6-1 |
| Todd Martin | m. | Chuck Adams | 6-2 7-6 |
| Brian Garrow | m. | Doug Flach | 6-3 7-5 |
| Steve Bryan | m. | Luke Jensen | 6-3 6-2 |
| Ville Jansson | m. | Nevio Devide | 6-4 6-3 |
| Robbie Weiss | m. | Steve Herdoiza | 6-2 6-3 |
| Scott Warner | m. | Malivai Washington | 7-5 6-4 |
Babak 32 besar
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Malivai Washington | m. | Paul Koscielski | 4-6 6-4 6-3 |
| Bryan Shelton | m. | Alex Obrien | 6-4 6-3 |
| Todd Martin | m. | Al Parker | 6-0 6-0 |
| Luke Jensen | m. | Martin Blackman | 7-5 6-4 |
| Ville Jansson | m. | Craig Boynton | 6-3 6-1 |
| Steve Herdoiza | m. | Miguel Dungo | 6-4 3-6 7-5 |
| Doug Flach | m. | Kent Kinnear | 3-6 6-4 6-3 |
| Buff Farrow | m. | Craig Campbell | 6-2 6-2 |
| Chuck Adams | m. | Malcolm Allen | 7-5 6-4 |
| Nevio Devide | m. | Charles Merzbacher | 7-6 7-6 |
| Tom Mercer | m. | Royce Deppe | 6-4 6-1 |
| Arkie Engle | m. | Doug Burke | 7-6 4-1 RET |
| Robbie Weiss | m. | Alberto Paris | 6-0 3-4 RET |
| Scott Warner | m. | Juan Farrow | 6-2 6-4 |
| Steve Bryan | m. | Peter Doohan | 6-1 6-2 |
| Brian Garrow | m. | Gianluca Pozzi | 6-2 2-6 6-3 |