Chicago 1988 WTA
Final
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Martina Navratilova | m. | Chris Evert | 6-2 6-2 |
Semifinal
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Martina Navratilova | m. | Helena Sukova | 6-4 6-3 |
| Chris Evert | m. | Manuela Maleeva Fragniere | 6-4 2-6 6-2 |
Perempat final
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Martina Navratilova | m. | Zina Garrison | 6-3 6-3 |
| Helena Sukova | m. | Gabriela Sabatini | 6-3 2-6 6-2 |
| Manuela Maleeva Fragniere | m. | Ann Grossman | 6-2 6-1 |
| Chris Evert | m. | Rosalyn Fairbank | 6-0 6-2 |
Babak 16 besar
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Martina Navratilova | m. | Amy Frazier | 6-0 6-3 |
| Zina Garrison | m. | Mareen Louie Harper | 6-3 6-2 |
| Gabriela Sabatini | m. | Kathy Rinaldi Stunkel | 6-0 6-2 |
| Helena Sukova | m. | Robin White | 6-4 6-4 |
| Ann Grossman | m. | Natalia Zvereva | 6-3 6-3 |
| Manuela Maleeva Fragniere | m. | Anne Smith | 7-6 6-2 |
| Rosalyn Fairbank | m. | Lori Mcneil | 5-7 6-3 6-2 |
| Chris Evert | m. | Stephanie Rehe | W/O |
Babak 32 besar
| Pemenang | Kalah | Skor | |
|---|---|---|---|
| Amy Frazier | m. | Helen Kelesi | 6-4 4-6 7-6 |
| Mareen Louie Harper | m. | Heather Ludloff | 7-6 6-4 |
| Zina Garrison | m. | Halle Cioffi | 6-3 6-3 |
| Kathy Rinaldi Stunkel | m. | Gigi Fernandez | 6-2 6-3 |
| Robin White | m. | Louise Allen | 6-3 4-6 6-2 |
| Helena Sukova | m. | Carrie Cunningham | 6-2 6-1 |
| Natalia Zvereva | m. | Angelica Gavaldon | 6-1 6-0 |
| Ann Grossman | m. | Mary Lou Piatek | 6-4 6-3 |
| Anne Smith | m. | Shaun Stafford | 6-3 6-4 |
| Lori Mcneil | m. | Claudia Kohde Kilsch | 6-4 6-1 |
| Rosalyn Fairbank | m. | Wendy Turnbull | 2-6 7-6 6-2 |
| Stephanie Rehe | m. | Larisa Savchenko | 3-6 6-4 7-6 |
Data: Jeff Sackmann / Tennis Abstract — CC BY-NC-SA 4.0