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