| Wimbledon Women | 07/01 15:55 | 23 | [143] Dalila Jakupovic v Kirsten Flipkens [103] | 1-6,3-6 | |
| WTA Eastbourne | 06/24 15:55 | 24 | [81] Kirsten Flipkens v Caroline Wozniacki [14] | 3-6,4-6 | |
| WTA Mallorca | 06/17 14:50 | 25 | [30] Sofia Kenin v Kirsten Flipkens [80] | 6-2,6-3 | |
| WTA Hertogenbosch | 06/14 16:55 | 27 | [69] Kirsten Flipkens v Elena Rybakina [134] | 4-6,4-6 | |
| WTA Hertogenbosch | 06/12 14:00 | 26 | [32] Lesia Tsurenko v Kirsten Flipkens [69] | 6-7,5-7 | |
| WTA Hertogenbosch | 06/11 09:00 | 25 | [69] Kirsten Flipkens v Aleksandra Krunic [66] | 6-3,3-6,6-1 | |
| French Open Women | 05/28 09:00 | 23 | [59] Monica Puig v Kirsten Flipkens [64] | 6-1,7-5 | |
| WTA Nurnberg | 05/22 08:30 | 25 | [93] Sorana Cirstea v Kirsten Flipkens [59] | 7-6,6-2 | |
| WTA Madrid | 05/04 12:35 | 24 | [59] Kirsten Flipkens v Anastasija Sevastova [13] | 6-0,3-6,2-6 | |
| WTA Rabat | 04/30 16:35 | 25 | [18] Elise Mertens v Kirsten Flipkens [59] | 6-3,6-1 | |
| WTA Istanbul | 04/24 08:00 | 25 | [59] Kirsten Flipkens v Ana Bogdan [150] | Retired | |
| 2019 Fed Cup - World Group Play Offs | 04/21 13:05 | - | Kirsten Flipkens v Carla Suarez Navarro | Cancelled | |
| 2019 Fed Cup | 04/20 11:30 | - | [59] Kirsten Flipkens v Garbine Muguruza [19] | 6-3,4-6,6-4 | |
| WTA Monterrey | 04/06 01:00 | 27 | [5] Angelique Kerber v Kirsten Flipkens [58] | 6-2,6-4 | |
| WTA Monterrey | 04/03 22:55 | 26 | [92] Dalila Jakupovic v Kirsten Flipkens [58] | 3-6,3-6 | |
| WTA Monterrey | 04/01 19:00 | 25 | [120] Olga Danilovic v Kirsten Flipkens [58] | 2-6,1-6 | |
| WTA Miami | 03/20 17:35 | 23 | [44] Yulia Putintseva v Kirsten Flipkens [56] | 4-6,6-4,7-5 | |
| WTA Indian Wells | 03/09 23:50 | 24 | [56] Kirsten Flipkens v Danielle Collins [25] | 4-6,1-6 | |
| WTA Indian Wells | 03/08 02:00 | 23 | [56] Kirsten Flipkens v Eugenie Bouchard [73] | 7-5,3-6,7-5 | |
| WTA Budapest | 02/19 11:15 | 25 | Evgeniya Rodina v Kirsten Flipkens | Cancelled | |
| WTA St. Petersburg | 01/28 10:00 | 25 | [52] Alison Van Uytvanck v Kirsten Flipkens [55] | 6-2,6-4 | |
| Australian Open Women | 01/14 08:15 | 23 | [50] Kirsten Flipkens v Aliaksandra Sasnovich [31] | 1-6,1-6 | |
| WTA Hobart | 01/10 02:00 | 27 | [56] Sofia Kenin v Kirsten Flipkens [49] | 7-5,7-5 | |
| WTA Hobart | 01/09 01:00 | 26 | [46] Viktoria Kuzmova v Kirsten Flipkens [49] | 7-6,4-6,1-6 | |
| WTA Hobart | 01/08 02:10 | 25 | [82] Dalila Jakupovic v Kirsten Flipkens [49] | 4-6,5-7 | |
| WTA Auckland | 01/01 23:00 | 26 | [86] Sara Sorribes Tormo v Kirsten Flipkens [47] | 6-4,1-6,6-1 | |
| WTA Auckland | 01/01 01:00 | 25 | [101] Sachia Vickery v Kirsten Flipkens [47] | 2-6,2-6 | |
| WTA Luxembourg | 10/17 11:00 | 26 | [47] Belinda Bencic v Kirsten Flipkens [52] | 6-1,6-3 | |
| WTA Luxembourg | 10/16 16:00 | 25 | [113] Mandy Minella v Kirsten Flipkens [52] | 2-6,3-6 | |
| WTA Luxembourg | 10/16 08:00 | 25 | Dayana Yastremska v Kirsten Flipkens | Cancelled |