First round completed and second round commenced in Chicago.
2021 Chicago Fall Tennis Classic - a WTA 500 tournament, on Hard, in Chicago, Illinois, USA, 27 September - 3 October 2021.
No defending champion:
This is a new tournament on the WTA calendar.
Lauren Davis withdrew after the main draw was published due to illness, and was replaced by lucky loser Harriet Dart.
First round results:
- Amanda Anisimova defeated Viktorija Golubic 6-0 5-7 6-4
- Elena-Gabriela Ruse defeated Camila Giorgi (15) 6-4 6-2
- Tereza Martincova defeated Maria Camila Osorio Serrano 6-3 7-5
- Tamara Zidansek (13) defeated Sloane Stephens 6-2 6-1
- Lucky loser Harriet Dart defeated qualifier Beatriz Haddad Maia 6-1 3-6 6-1
- Jil Teichmann (16) defeated Kaia Kanepi 7-6(3) 7-5
- Magda Linette defeated wildcard CoCo Vandeweghe 6-1 6-4
- Anett Kontaveit (11) defeated Madison Brengle 6-4 6-3
- Victoria Azarenka (14) defeated Zhang Shuai 6-2 6-1
- Wildcard Hailey Baptiste defeated Jasmine Paolini 7-5 6-3
Second round results:
- Ons Jabeur (6) defeated Hsieh Su-wei 6-1 6-0
- Elise Mertens (7) defeated Dayana Yastremska 6-1 6-3
- Danielle Collins (10) defeated Misaki Doi 4-6 6-3 7-5
- Garbiñe Muguruza (2) defeated Ann Li 6-4 6-4
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