| WTA - Linz | 10/10 10:00 | 25 | [51] Flipkens, Kirsten v Srtycova, Barbora [29] | 6-7,6-7 | |
| Pékin, Chine | 10/02 06:45 | 25 | [57] Flipkens, Kirsten v Bertens, Kiki [11] | 1-6,1-6 | |
| Pékin, Chine | 09/30 10:45 | 24 | [58] Flipkens, Kirsten v Katie Boulter [108] | 4-6,6-2,7-5 | |
| Wuhan, China | 09/23 03:00 | 24 | [46] Monica Puig v Flipkens, Kirsten [57] | 7-5,5-7,6-3 | |
| WTA Seoul | 09/19 03:00 | 26 | [57] Flipkens, Kirsten v Rodina, Evgeniya [84] | 4-6,6-4,5-7 | |
| WTA Seoul | 09/18 03:00 | 25 | Flipkens, Kirsten v Sohyun Park | 6-0,6-2 | |
| US Open Women | 08/30 20:15 | 24 | [49] Aleksandra Krunic v Flipkens, Kirsten [57] | 6-1,6-3 | |
| US Open Women | 08/28 16:35 | 23 | [57] Flipkens, Kirsten v Vandeweghe, Coco [25] | 6-3,7-6 | |
| New Haven, USA | 08/18 20:00 | 45 | [48] Flipkens, Kirsten v Tamara Zidansek [74] | 3-6,2-6 | |
| New Haven, USA | 08/17 17:20 | 44 | Flipkens, Kirsten v Davis, Emma | 6-3,6-1 | |
| WTA Cincinnati Qual | 08/11 22:30 | 44 | Flipkens, Kirsten v Vikhlyantseva, Natalia | 3-6,3-6 | |
| WTA Montreal | 08/08 00:25 | 24 | [191] Abanda, Francoise v Flipkens, Kirsten [47] | 6-3,6-2 | |
| WTA Montreal Qual | 08/05 18:30 | 45 | [45] Flipkens, Kirsten v S. Hlavackova, A. [7] | 1-6,6-1,6-2 | |
| WTA Montreal Qual | 08/04 22:35 | 44 | Flipkens, Kirsten v Mattek-Sands, Bethanie | 6-1,6-4 | |
| Wimbledon Women | 07/05 17:10 | 24 | [12] Jelena Ostapenko v Flipkens, Kirsten [45] | 6-1,6-3 | |
| Wimbledon Women | 07/03 17:50 | 23 | [111] Heather Watson v Flipkens, Kirsten [45] | 4-6,5-7 | |
| ITF Women Southsea | 06/29 10:00 | 29 | [144] Katie Boulter v Flipkens, Kirsten [51] | 4-6,7-5,3-6 | |
| ITF Women Southsea | 06/28 10:00 | 28 | [71] Parmentier, Pauline v Flipkens, Kirsten [51] | 3-6,2-6 | |
| ITF Women Southsea | 06/27 10:00 | 27 | [84] Lapko, Vera v Flipkens, Kirsten [51] | 3-6,6-3,4-6 | |
| ITF Women Southsea | 06/26 10:00 | 26 | [67] Kozlova, Kateryna v Flipkens, Kirsten [51] | 2-6,3-6 | |
| WTA Mallorca | 06/19 08:00 | - | Flipkens, Kirsten v Aliaksandra Sasnovich | Cancelled | |
| WTA Hertogenbosch | 06/17 10:00 | 29 | [55] Aleksandra Krunic v Flipkens, Kirsten [60] | 6-7,7-5,6-1 | |
| WTA Hertogenbosch | 06/16 11:55 | 28 | [60] Flipkens, Kirsten v Kuzmova, Viktoria [81] | 7-5,6-7,6-4 | |
| WTA Hertogenbosch | 06/15 12:55 | 27 | [46] Aryna Sabalenka v Flipkens, Kirsten [60] | 4-6,4-6 | |
| WTA Hertogenbosch | 06/15 09:00 | 26 | [60] Flipkens, Kirsten v Bertens, Kiki [21] | 6-4,6-7,6-1 | |
| WTA Hertogenbosch | 06/12 12:15 | 25 | [142] Anna Kalinskaya v Flipkens, Kirsten [60] | 3-6,0-6 | |
| French Open Women | 05/30 17:50 | 24 | [14] Daria Kasatkina v Flipkens, Kirsten [65] | 6-3,6-3 | |
| French Open Women | 05/28 13:40 | 23 | [64] Tatjana Maria v Flipkens, Kirsten [69] | 6-7,4-6 | |
| Nuremberg, Germany | 05/25 15:00 | 28 | [105] Alison Riske v Flipkens, Kirsten [69] | 6-3,6-1 | |
| Nuremberg, Germany | 05/25 08:45 | 27 | [18] Bertens, Kiki v Flipkens, Kirsten [69] | 7-5,3-6,6-7 |