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