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