Chicago 1986 WTA
Final
| Winner | Loser | Score | |
|---|---|---|---|
| Martina Navratilova | d. | Hana Mandlikova | 7-5 7-5 |
Semifinals
| Winner | Loser | Score | |
|---|---|---|---|
| Martina Navratilova | d. | Zina Garrison | 6-2 7-5 |
| Hana Mandlikova | d. | Pam Shriver | 6-4 3-6 7-5 |
Quarterfinals
| Winner | Loser | Score | |
|---|---|---|---|
| Martina Navratilova | d. | Gabriela Sabatini | 6-2 7-6 |
| Zina Garrison | d. | Katerina Maleeva | 7-5 6-1 |
| Pam Shriver | d. | Kathy Rinaldi Stunkel | 6-3 6-4 |
| Hana Mandlikova | d. | Claudia Kohde Kilsch | 6-4 7-5 |
Round of 16
| Winner | Loser | Score | |
|---|---|---|---|
| Martina Navratilova | d. | Bettina Bunge | 6-4 6-0 |
| Gabriela Sabatini | d. | Kate Gompert | 6-4 6-1 |
| Katerina Maleeva | d. | Helena Sukova | 7-5 6-1 |
| Zina Garrison | d. | Alycia Moulton | 4-6 6-4 7-5 |
| Kathy Rinaldi Stunkel | d. | Tine Scheuer Larsen | 6-7 7-5 6-2 |
| Pam Shriver | d. | Barbara Potter | 6-3 6-4 |
| Claudia Kohde Kilsch | d. | Anne White | 6-3 6-3 |
| Hana Mandlikova | d. | Melissa Gurney | 6-4 6-2 |
Round of 32
| Winner | Loser | Score | |
|---|---|---|---|
| Bettina Bunge | d. | Terry Phelps | 6-3 6-2 |
| Kate Gompert | d. | Ann Henricksson | 6-1 6-3 |
| Gabriela Sabatini | d. | Larisa Savchenko | 6-0 7-5 |
| Katerina Maleeva | d. | Catarina Lindqvist Ryan | 7-6 6-1 |
| Alycia Moulton | d. | Elise Burgin | 6-2 6-7 6-1 |
| Zina Garrison | d. | Pam Casale | 6-4 6-1 |
| Kathy Rinaldi Stunkel | d. | Robin White | 7-6 6-4 |
| Tine Scheuer Larsen | d. | Helen Kelesi | 6-2 7-5 |
| Barbara Potter | d. | Rosalyn Fairbank | 6-3 6-2 |
| Claudia Kohde Kilsch | d. | Dianne Fromholtz | 6-3 6-4 |
| Anne White | d. | Laura Arraya | 6-4 6-1 |
| Melissa Gurney | d. | Mary Joe Fernandez | 6-4 6-1 |
Data: Jeff Sackmann / Tennis Abstract — CC BY-NC-SA 4.0