| Wimbledon Women | 06/30 16:00 | 24 | [190] Kirsten Flipkens v Simona Halep [18] | 5-7,4-6 | |
| Wimbledon Women | 06/28 13:50 | 23 | [190] Kirsten Flipkens v Jaimee Fourlis [150] | 7-5,6-2 | |
| WTA Eastbourne | 06/22 10:00 | 26 | [257] Kirsten Flipkens v Viktoriya Tomova [128] | 6-3,3-6,4-6 | |
| WTA Eastbourne | 06/21 10:00 | 25 | [30] Elise Mertens v Kirsten Flipkens [257] | 2-6,6-2,1-6 | |
| WTA Eastbourne | 06/20 12:25 | 24 | [68] Maryna Zanevska v Kirsten Flipkens [257] | 2-6,3-6 | |
| WTA Eastbourne | 06/19 13:00 | 19 | [129] Viktoriya Tomova v Kirsten Flipkens [252] | 6-4,2-6,6-7 | |
| WTA Eastbourne | 06/18 10:30 | 14 | [252] Kirsten Flipkens v Kristina Mladenovic [115] | 6-4,6-4 | |
| WTA Hertogenbosch | 06/10 14:00 | 27 | [42] Shelby Rogers v Kirsten Flipkens [308] | 3-6,6-1,6-4 | |
| WTA Hertogenbosch | 06/09 12:30 | 26 | [308] Kirsten Flipkens v Ann Li [68] | 6-1,6-1 | |
| WTA Hertogenbosch | 06/07 16:35 | 25 | [308] Kirsten Flipkens v Anastasia Tikhonova [175] | 6-2,5-7,6-3 | |
| WTA Miami | 03/23 22:15 | 23 | [315] Kirsten Flipkens v Viktorija Golubic [42] | 4-6,6-4,4-6 | |
| WTA Miami | 03/22 16:35 | 19 | [315] Kirsten Flipkens v Alycia Parks [155] | 7-5,6-1 | |
| WTA Miami | 03/21 16:55 | 14 | [98] Diane Parry v Kirsten Flipkens [315] | 6-4,4-6,5-7 | |
| WTA Indian Wells | 03/08 22:35 | 19 | [333] Kirsten Flipkens v Catherine McNally [172] | 5-7,6-3,4-6 | |
| WTA Indian Wells | 03/07 19:00 | 14 | [92] Lauren Davis v Kirsten Flipkens [333] | 5-7,3-6 | |
| WTA Doha | 02/19 10:40 | 19 | [63] Aliaksandra Sasnovich v Kirsten Flipkens [324] | 6-3,6-2 | |
| WTA Doha | 02/18 09:30 | 14 | [324] Kirsten Flipkens v Astra Sharma [87] | 5-7,6-1,6-3 | |
| WTA Dubai | 02/13 13:40 | 19 | [35] Jil Teichmann v Kirsten Flipkens [327] | 6-0,6-2 | |
| WTA Dubai | 02/12 14:10 | 14 | [286] Diana Marcinkevica v Kirsten Flipkens [327] | 0-6,3-6 | |
| Australian Open Women | 01/17 01:25 | 23 | [35] Sara Sorribes Tormo v Kirsten Flipkens [326] | 6-4,6-1 | |
| WTA Adelaide 2 | 01/10 03:10 | 19 | [314] Kirsten Flipkens v Storm Sanders [135] | 3-6,4-6 | |
| WTA Adelaide 2 | 01/09 02:35 | 14 | [94] Katarzyna Piter v Kirsten Flipkens [311] | 2-6,0-6 | |
| WTA Adelaide 2 | 01/09 02:25 | 45 | Ana Konjuh v Kirsten Flipkens | Cancelled | |
| WTA Tenerife | 10/17 10:00 | 19 | [120] Stefanie Voegele v Kirsten Flipkens [132] | 6-3,7-6 | |
| WTA Tenerife | 10/16 09:30 | 14 | [284] Cristiana Ferrando v Kirsten Flipkens [132] | 6-4,5-7,3-6 | |
| WTA Indian Wells | 10/07 18:00 | 23 | [59] Caroline Garcia v Kirsten Flipkens [132] | 5-7,6-4,6-0 | |
| WTA Indian Wells | 10/05 21:25 | 19 | [132] Kirsten Flipkens v Katarzyna Kawa [163] | 2-6,6-2,6-3 | |
| WTA Indian Wells | 10/04 19:40 | 14 | Kirsten Flipkens v Theadora Rabman | 5-7,7-6,6-1 | |
| WTA Chicago | 09/27 17:20 | 24 | [135] Kirsten Flipkens v Danielle Collins [28] | 4-6,2-6 | |
| WTA Chicago | 09/26 18:05 | - | [137] Kirsten Flipkens v Rebecca Marino [158] | 6-4,6-7,6-4 |