WTA Chicago singles and doubles draws with all head to head stats.
| Rank | W |
| Country | |
| Start Date | 12.02.1990 |
| Surfaces | |
| Prize Money |
![]() | Martina Navratilova | 1990 |
![]() | Martina Navratilova | 12 | |
![]() | Catherine Wolf | 4 | |
![]() | Dorothy Levine | 2 | |
![]() | Margaret Court | 2 | |
![]() | Magdalena Maleeva | 1 |
Women's Singles
Women's Qualifying Singles
| Players | player 1 | player 2 | scr | h2h | |||
| Unknown | |||||||
6 1 6 2 | H2H 8-12 | ||||||
6 3 7 5 | H2H 40-9 | ||||||
6 1 6 0 | H2H 16-5 | ||||||
6 0 6 1 | H2H 8-0 | ||||||
| Final | |||||||
6 3 6 2 | H2H 44-12 | ||||||
| Semifinals | |||||||
6 4 6 3 | H2H 104-3 | ||||||
6 2 6 0 | H2H 16-5 | ||||||
| Fourth | |||||||
6 4 6 4 | H2H 12-8 | ||||||
6 3 6 2 | H2H 21-29 | ||||||
6 3 3 6 6 3 | H2H 5-14 | ||||||
6 0 6 0 | H2H 5-0 | ||||||
0 6 6 4 6 3 | H2H 8-0 | ||||||
6 4 7 5 | H2H 8-4 | ||||||
6 1 6 7 7 5 | H2H 8-4 | ||||||
6 3 6 4 | H2H 4-0 | ||||||
| Third | |||||||
7 5 3 6 6 1 | H2H 8-1 | ||||||
6 4 6 4 | H2H 9-4 | ||||||
6 3 6 4 | H2H 4-9 | ||||||
6 1 6 3 | H2H 12-0 | ||||||
6 3 1 6 6 4 | H2H 8-4 | ||||||
6 1 6 7 6 4 | H2H 12-4 | ||||||
6 3 7 6 | H2H 4-8 | ||||||
3 6 6 3 6 1 | H2H 12-0 | ||||||
6 2 6 2 | H2H 19-4 | ||||||
3 6 6 3 6 1 | H2H 4-0 | ||||||
6 3 6 3 | H2H 8-0 | ||||||
7 5 7 6 | H2H 8-12 | ||||||
1 6 6 1 7 6 | H2H 12-0 | ||||||
7 6 7 6 | H2H 2-0 | ||||||
6 4 6 1 | H2H 8-0 | ||||||
7 5 7 6 | H2H 16-4 | ||||||