Stadium: Stadium 4 Round: 14 Ground: Hardcourt outdoor
| WTA Chicago | 2021/09/27 17:20 | Flipkens, Kirsten v Collins, Danielle | 4-6,2-6 |
| WTA Chicago | 2021/09/26 18:05 | Flipkens, Kirsten v Rebecca Marino | 6-4,6-7,6-4 |
| WTA - Miami | 2021/03/25 17:30 | Jelena Ostapenko v Flipkens, Kirsten | 6-2,5-7,6-3 |
| WTA - Miami | 2021/03/23 14:00 | Flipkens, Kirsten v Bolsova Zadoinov, Aliona | 4-6,3-6 |
| WTA - Miami | 2021/03/22 14:00 | Flipkens, Kirsten v Whitney Osuigwe | 4-6,6-3,6-1 |
| WTA St. Petersburg | 2021/03/16 14:10 | Katerina Siniakova v Flipkens, Kirsten | 6-1,6-2 |
| Open d'Australie - Femmes | 2021/02/08 00:00 | Flipkens, Kirsten v Venus Williams | 5-7,2-6 |
| WTA - Abu Dhabi | 2021/01/06 10:40 | Laura Siegemund v Flipkens, Kirsten | 7-5,5-7,4-6 |
| UTR Pro Tennis Series New York Women | 2021/08/28 17:30 | Theadora Rabman v Clarissa Hand | 6-4,5-2 |
| UTR Pro Tennis Series New York Women | 2021/08/28 12:00 | Theadora Rabman v Daria Smetannikov | 7-6,0-6,6-6 |
| UTR Pro Tennis Series New York Women | 2021/08/26 18:30 | Theadora Rabman v Livianu, Jessica | 1-6,1-6 |
| UTR Pro Tennis Series New York Women | 2021/08/25 20:00 | Theadora Rabman v Riley, Alexandra | 6-4,5-1 |
| UTR Pro Tennis Series New York Women | 2021/08/24 20:00 | Nathalie Rodilosso v Theadora Rabman | 2-6,6-6 |