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