Stadium: Centre Court
| Billie Jean King Cup | 2021/11/02 20:00 | Dolehide/Vandeweghe v Kuzmova/Mihalikova | 2-6,7-6,10-12 |
| WTA Chicago - NP | 2021/10/03 19:40 | Peschke/Petkovic v Dolehide/Vandeweghe | 6-3,6-1 |
| WTA Chicago - NP | 2021/10/02 16:00 | Dolehide/Vandeweghe v Jurak/Klepac | 6-3,6-4 |
| WTA Chicago - NP | 2021/10/01 18:40 | Dolehide/Vandeweghe v Kudermetova/Mattek-Sands | 6-2,6-3 |
| WTA Chicago - NP | 2021/09/30 19:15 | Bouzkova/Hradecka v Dolehide/Vandeweghe | 3-6,2-6 |
| WTA Chicago - NP | 2021/09/29 19:25 | Dolehide/Vandeweghe v Mirza/Zhang | 6-1,5-7,10-6 |